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Volumn 9, Issue 1, 2003, Pages 9-35

Diketopiperazines in peptide and combinatorial chemistry

Author keywords

Combinatorial chemistry; Diketopiperazine; DKP; Peptide cyclization; Piperazine 2,5 dione; Side reaction; SPOC; SPPS

Indexed keywords

AMINO ACID; BENZODIAZEPINE DERIVATIVE; CYCLOPEPTIDE; DEMETHOXYFUMITREMORGIN C; HYDANTOIN DERIVATIVE; PEPTIDE DERIVATIVE; PIPERAZINE DERIVATIVE; PIPERAZINEDIONE; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

EID: 0037265516     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.446     Document Type: Review
Times cited : (178)

References (217)
  • 1
    • 0016593869 scopus 로고
    • Naturally occurring 2,5-dioxopiperazines and related compounds
    • Springer-Verlag: Vienna
    • Sammes PG. Naturally occurring 2,5-dioxopiperazines and related compounds. In Fortschritte der Chemie Organischer Naturstoffe. Springer-Verlag: Vienna, 1975; 51-118.
    • (1975) Fortschritte Der Chemie Organischer Naturstoffe , pp. 51-118
    • Sammes, P.G.1
  • 2
    • 0000310917 scopus 로고
    • The cyclic dipeptides. Proper model compounds in peptide research
    • Anteunis MJO. The cyclic dipeptides. Proper model compounds in peptide research. Bull. Soc. Chim. Belg. 1978; 87: 627-650.
    • (1978) Bull. Soc. Chim. Belg. , vol.87 , pp. 627-650
    • Anteunis, M.J.O.1
  • 3
    • 0000083388 scopus 로고
    • Piperazine-2,5-diones and related lactim ethers
    • Academic Press: San Diego, CA
    • Rajappa S, Natekar MV. Piperazine-2,5-diones and related lactim ethers. In Advances in Heterocyclic Chemistry. Academic Press: San Diego, CA, 1993; 187-289.
    • (1993) Advances in Heterocyclic Chemistry , pp. 187-289
    • Rajappa, S.1    Natekar, M.V.2
  • 4
    • 0030132929 scopus 로고    scopus 로고
    • Structurally homogeneous and heterogeneous synthetic combinatorial libraries
    • Krchnak V, Weichsel AS, Cabel D, Flegelova Z, Lebl M. Structurally homogeneous and heterogeneous synthetic combinatorial libraries. Mol. Div. 1996; 1: 149-164.
    • (1996) Mol. Div. , vol.1 , pp. 149-164
    • Krchnak, V.1    Weichsel, A.S.2    Cabel, D.3    Flegelova, Z.4    Lebl, M.5
  • 5
    • 0035512309 scopus 로고    scopus 로고
    • Solid-phase synthesis of substituted imidazoline-tethered 2,3-diketopiperazines, cyclic ureas, and cyclic thioureas
    • Acharya AN, Ostresh JM, Houghten RA. Solid-phase synthesis of substituted imidazoline-tethered 2,3-diketopiperazines, cyclic ureas, and cyclic thioureas. J. Comb. Chem. 2001; 3: 612-623.
    • (2001) J. Comb. Chem. , vol.3 , pp. 612-623
    • Acharya, A.N.1    Ostresh, J.M.2    Houghten, R.A.3
  • 6
    • 0013086377 scopus 로고
    • Ueber eine neue Verwandlung des Leucins
    • Kohler A. Ueber eine neue Verwandlung des Leucins. Liebigs Ann. Chem. 1865; 134: 367-372.
    • (1865) Liebigs Ann. Chem. , vol.134 , pp. 367-372
    • Kohler, A.1
  • 7
    • 84945084007 scopus 로고
    • Ueber einige Derivate des Glykocolls
    • Fischer E, Forneau E. Ueber einige Derivate des Glykocolls. Chem. Ber. 1901; 34: 2868-2877.
    • (1901) Chem. Ber. , vol.34 , pp. 2868-2877
    • Fischer, E.1    Forneau, E.2
  • 8
    • 0013038986 scopus 로고
    • Einiges ueber Albumin, Casein und Fibrin
    • Bopp F. Einiges ueber Albumin, Casein und Fibrin. Liebigs Ann. Chem. 1849; 69: 16-37.
    • (1849) Liebigs Ann. Chem. , vol.69 , pp. 16-37
    • Bopp, F.1
  • 9
    • 84981834983 scopus 로고
    • Ueber das Bromoacetortholuid und einige daraus erhaltene Verbindungen
    • Abenius PW, Widman O. Ueber das Bromoacetortholuid und einige daraus erhaltene Verbindungen. Chem. Ber. 1888; 21: 1662-1664.
    • (1888) Chem. Ber. , vol.21 , pp. 1662-1664
    • Abenius, P.W.1    Widman, O.2
  • 10
    • 0013130995 scopus 로고
    • Ueber das Glycocoll
    • Curtius T. Ueber das Glycocoll. Chem. Ber. 1883; 16: 753-757.
    • (1883) Chem. Ber. , vol.16 , pp. 753-757
    • Curtius, T.1
  • 11
    • 0013093481 scopus 로고
    • Ueber Glycinanhydrid und seine Verbindungen
    • Curtius T, Goebel F. Ueber Glycinanhydrid und seine Verbindungen. J. Prakt. Chem. 1888; 37: 173-181.
    • (1888) J. Prakt. Chem. , vol.37 , pp. 173-181
    • Curtius, T.1    Goebel, F.2
  • 12
  • 13
    • 0013086546 scopus 로고
    • Acid-catalyzed decarbobenzyloxylation
    • Albertson NF, McKay FC. Acid-catalyzed decarbobenzyloxylation. J. Am. Chem. Soc. 1953; 75: 5323-5326.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 5323-5326
    • Albertson, N.F.1    McKay, F.C.2
  • 15
    • 0017295221 scopus 로고
    • A method for sequencing peptides: A co-operation of diphenyl phosphorazidate and 2-mercapto- or 2-hydroxypyridine for N-acyldiketopiperazine formation
    • Yamada S, Yokoyama Y, Shioiri T. A method for sequencing peptides: a co-operation of diphenyl phosphorazidate and 2-mercapto- or 2-hydroxypyridine for N-acyldiketopiperazine formation. Experientia 1976; 32: 398-399.
    • (1976) Experientia , vol.32 , pp. 398-399
    • Yamada, S.1    Yokoyama, Y.2    Shioiri, T.3
  • 16
    • 0013039319 scopus 로고
    • The anhydrides of basic amino-acids
    • Adamson DW. The anhydrides of basic amino-acids. J. Chem. Soc. 1943; 39-40.
    • (1943) J. Chem. Soc. , pp. 39-40
    • Adamson, D.W.1
  • 18
    • 33947302252 scopus 로고
    • Simple route to sterically pure dioxopiperazines
    • Nitecki DE, Halpern B, Westley JW. Simple route to sterically pure dioxopiperazines. J. Org. Chem. 1968; 33: 864-866.
    • (1968) J. Org. Chem. , vol.33 , pp. 864-866
    • Nitecki, D.E.1    Halpern, B.2    Westley, J.W.3
  • 19
    • 0018436849 scopus 로고
    • Cyclic peptides. VI. Asymmetric hydrogenation of dehydroalanine or dehydroaminobutanoic acid residue in cyclodipeptides
    • Lee S, Kanmera T, Aoyagi H, Izumiya N. Cyclic peptides. VI. Asymmetric hydrogenation of dehydroalanine or dehydroaminobutanoic acid residue in cyclodipeptides. Int. J. Peptide Protein Res. 1979; 13: 207-217.
    • (1979) Int. J. Peptide Protein Res. , vol.13 , pp. 207-217
    • Lee, S.1    Kanmera, T.2    Aoyagi, H.3    Izumiya, N.4
  • 20
    • 0014247909 scopus 로고
    • Covenient synthesis of 2,5-piperazinediones
    • Kopple KD, Ghazarian HG. Covenient synthesis of 2,5-piperazinediones. J. Org. Chem. 1968; 33: 862-864.
    • (1968) J. Org. Chem. , vol.33 , pp. 862-864
    • Kopple, K.D.1    Ghazarian, H.G.2
  • 21
    • 0013133483 scopus 로고
    • The behavior of peptides when heated in β-naphthol
    • Lichtenstein N. The behavior of peptides when heated in β-naphthol. J. Am. Chem. Soc. 1938; 60: 560-563.
    • (1938) J. Am. Chem. Soc. , vol.60 , pp. 560-563
    • Lichtenstein, N.1
  • 22
    • 0001463251 scopus 로고
    • Facile synthesis of cyclic dipeptides and detection of racemization
    • Ueda T, Saito M, Kato T, Izumiya N. Facile synthesis of cyclic dipeptides and detection of racemization. Bull. Chem. Soc. Jpn 1983; 56: 568-572.
    • (1983) Bull. Chem. Soc. Jpn , vol.56 , pp. 568-572
    • Ueda, T.1    Saito, M.2    Kato, T.3    Izumiya, N.4
  • 24
    • 0027372195 scopus 로고
    • An improved synthesis of the diketopiperazine catalyst cyclo[(S)-His-(S)-Phe]
    • Iyer MS, Lipton MA. An improved synthesis of the diketopiperazine catalyst cyclo[(S)-His-(S)-Phe]. Bioorg. Med. Chem. Lett. 1993; 3: 2061-2062.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 2061-2062
    • Iyer, M.S.1    Lipton, M.A.2
  • 25
    • 0001622386 scopus 로고
    • Enantioselective synthesis of non-proteinogenic amino acids via metallated bis-lactim ethers of 2,5-diketopiperazines
    • Schoellkopf U. Enantioselective synthesis of non-proteinogenic amino acids via metallated bis-lactim ethers of 2,5-diketopiperazines. Tetrahedron 1983; 39: 2085-2091.
    • (1983) Tetrahedron , vol.39 , pp. 2085-2091
    • Schoellkopf, U.1
  • 26
    • 0002527189 scopus 로고
    • A novel synthesis of N-carboxy-α-amino acid anhydride
    • Oya M, Katakai R, Nakai H. A novel synthesis of N-carboxy-α-amino acid anhydride. Chem. Lett. 1973; 1143-1144.
    • (1973) Chem. Lett. , pp. 1143-1144
    • Oya, M.1    Katakai, R.2    Nakai, H.3
  • 27
    • 45549112115 scopus 로고
    • The preparation of N-carboxyan-hydrides of α-amino acids using bis(trichloromethyl)-carbonate
    • Daly WH, Poche D. The preparation of N-carboxyan-hydrides of α-amino acids using bis(trichloromethyl)-carbonate. Tetrahedron Lett. 1988; 29: 5859-5862.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5859-5862
    • Daly, W.H.1    Poche, D.2
  • 28
    • 0029008119 scopus 로고
    • Synthesis and structural study of piperazine-2,5-diones derived from (R)-cysteine
    • González A, Vorob'eva SL, Linares A. Synthesis and structural study of piperazine-2,5-diones derived from (R)-cysteine. Tetrahedron: Asymmetry 1995; 6: 1357-1366.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 1357-1366
    • González, A.1    Vorob'eva, S.L.2    Linares, A.3
  • 30
    • 0025766607 scopus 로고
    • The stereospecific preparation of an hydroxyethylene isostere precursor via a novel piperidine-2,5-dione template
    • Plata DJ, Leanna MR, Morton HE. The stereospecific preparation of an hydroxyethylene isostere precursor via a novel piperidine-2,5-dione template. Tetrahedron Lett. 1991; 32: 3623-3626.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3623-3626
    • Plata, D.J.1    Leanna, M.R.2    Morton, H.E.3
  • 31
    • 0001424464 scopus 로고
    • Peptide synthesis via amino acid active esters. II. Some abnormal reactions during peptide synthesis
    • Goodman M, Steuben KC. Peptide synthesis via amino acid active esters. II. Some abnormal reactions during peptide synthesis. J. Am. Chem. Soc. 1962; 84: 1279-1283.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 1279-1283
    • Goodman, M.1    Steuben, K.C.2
  • 32
    • 0029928809 scopus 로고    scopus 로고
    • Stereoselective synthesis of N,N'-diaryl-2,5-dioxopiperazines from homochiral or racemic 2-bromopropananilides
    • D'Angeli F, Marchetti P, Rondanin R, Bertolasi V. Stereoselective synthesis of N,N'-diaryl-2,5-dioxopiperazines from homochiral or racemic 2-bromopropananilides. J. Org. Chem. 1996; 61: 1252-1255.
    • (1996) J. Org. Chem. , vol.61 , pp. 1252-1255
    • D'Angeli, F.1    Marchetti, P.2    Rondanin, R.3    Bertolasi, V.4
  • 33
    • 0000291413 scopus 로고
    • A synthesis of cyclic peptides utilizing high molecular weight carriers
    • Fridkin M, Patchornik A, Katchalski E. A synthesis of cyclic peptides utilizing high molecular weight carriers. J. Am. Chem. Soc. 1965; 87: 4646-4648.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 4646-4648
    • Fridkin, M.1    Patchornik, A.2    Katchalski, E.3
  • 34
    • 0014805953 scopus 로고
    • Synthesis of cyclic peptides on dual function supports
    • Flanigan E, Marschall GR. Synthesis of cyclic peptides on dual function supports. Tetrahedron Lett. 1970; 2403-2406.
    • (1970) Tetrahedron Lett. , pp. 2403-2406
    • Flanigan, E.1    Marschall, G.R.2
  • 35
    • 0021858148 scopus 로고
    • The use of Nbb resin in cyclic dipeptide ('diketopiperazine') synthesis
    • Giralt E, Eritja R, Josa J, Kuklinski C, Pedroso E. The use of Nbb resin in cyclic dipeptide ('diketopiperazine') synthesis. Synthesis 1985; 181-184.
    • (1985) Synthesis , pp. 181-184
    • Giralt, E.1    Eritja, R.2    Josa, J.3    Kuklinski, C.4    Pedroso, E.5
  • 37
    • 0030581332 scopus 로고    scopus 로고
    • Solid phase synthesis of a diketopiperazine catalyst containing the unnatural amino acid (S)-norarginine
    • Kowalski J, Lipton MA. Solid phase synthesis of a diketopiperazine catalyst containing the unnatural amino acid (S)-norarginine. Tetrahedron Lett. 1996; 37: 5839-5840.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5839-5840
    • Kowalski, J.1    Lipton, M.A.2
  • 38
    • 0017088666 scopus 로고
    • An explanation for the rare occurrence of cis peptide units in proteins and polypeptides
    • Ramachandran GN, Mitra AK. An explanation for the rare occurrence of cis peptide units in proteins and polypeptides. J. Mol. Biol. 1976; 107: 85-92.
    • (1976) J. Mol. Biol. , vol.107 , pp. 85-92
    • Ramachandran, G.N.1    Mitra, A.K.2
  • 39
    • 0024286073 scopus 로고
    • Influences of solvent water on protein folding: Free energies of solvation of cis and trans peptides are nearly identical
    • Radzicka A, Pedersen L, Wolfenden R. Influences of solvent water on protein folding: free energies of solvation of cis and trans peptides are nearly identical. Biochemistry 1988; 27: 4538-4541.
    • (1988) Biochemistry , vol.27 , pp. 4538-4541
    • Radzicka, A.1    Pedersen, L.2    Wolfenden, R.3
  • 40
    • 0001367406 scopus 로고
    • Mechanism of cis-trans isomerization of amide and peptide excited states
    • Li Y, Garrell RL, Houk KN. Mechanism of cis-trans isomerization of amide and peptide excited states. J. Am. Chem. Soc. 1991; 113: 5895-5896.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5895-5896
    • Li, Y.1    Garrell, R.L.2    Houk, K.N.3
  • 41
    • 0025299887 scopus 로고
    • Occurrence and role of cis peptide bonds in protein structure
    • Stewart DE, Sarkar A, Wampler JE. Occurrence and role of cis peptide bonds in protein structure. J. Mol. Biol. 1990; 214: 253-260.
    • (1990) J. Mol. Biol. , vol.214 , pp. 253-260
    • Stewart, D.E.1    Sarkar, A.2    Wampler, J.E.3
  • 42
    • 0028670805 scopus 로고
    • Cis-trans isomerization of the proline dipeptide
    • Fischer S, Dunbrack RL, Karplus M. Cis-trans isomerization of the proline dipeptide. J. Am. Chem. Soc. 1994; 116: 11931-11937.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 11931-11937
    • Fischer, S.1    Dunbrack, R.L.2    Karplus, M.3
  • 43
    • 0015492764 scopus 로고
    • Carboxyl-catalyzed intramolecular aminolysis. A side reaction in solid-phase peptide synthesis
    • Gisin RF, Merrifield RB. Carboxyl-catalyzed intramolecular aminolysis. A side reaction in solid-phase peptide synthesis. J. Am. Chem. Soc. 1972; 94: 3102-3106.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 3102-3106
    • Gisin, R.F.1    Merrifield, R.B.2
  • 44
    • 0016239989 scopus 로고
    • Nebenreaktionen bei der Festphasensynthese von Peptiden, IV. Intrachenare und interchenare aminolyse der Benzylesterverbindung zum polymeren Traeger und ihre Auswirkungen
    • Rothe M, Mazanek J. Nebenreaktionen bei der Festphasensynthese von Peptiden, IV. Intrachenare und interchenare aminolyse der Benzylesterverbindung zum polymeren Traeger und ihre Auswirkungen. Liebigs Ann. Chem. 1974; 439-459.
    • (1974) Liebigs Ann. Chem. , pp. 439-459
    • Rothe, M.1    Mazanek, J.2
  • 46
    • 0015969426 scopus 로고
    • Blocked α-amino groups in peptides due to diketopiperazine formation
    • Jornvall H. Blocked α-amino groups in peptides due to diketopiperazine formation. FEBS Lett. 1974; 38: 329-333.
    • (1974) FEBS Lett. , vol.38 , pp. 329-333
    • Jornvall, H.1
  • 47
    • 0018623326 scopus 로고
    • Formation of aminosuccinyl peptides during acidolytic deprotection followed by their transformation to piperazine-2,5-dione derivatives in neutral media
    • Schoen I, Kisfaludy L. Formation of aminosuccinyl peptides during acidolytic deprotection followed by their transformation to piperazine-2,5-dione derivatives in neutral media. Int. J. Peptide Protein Res. 1979; 14: 485-494.
    • (1979) Int. J. Peptide Protein Res. , vol.14 , pp. 485-494
    • Schoen, I.1    Kisfaludy, L.2
  • 48
    • 0013085307 scopus 로고
    • Cyclization under mild conditions of cysteine containing peptides
    • Zanotti G, Pinnen F, Lucente G. Cyclization under mild conditions of cysteine containing peptides. Tetrahedron Lett. 1985; 26: 5481-5484.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5481-5484
    • Zanotti, G.1    Pinnen, F.2    Lucente, G.3
  • 50
    • 0001393548 scopus 로고
    • Studies of multivalent amino acids and peptides. VIII. The synthesis of bisanhydro-L-cystinyl-L-cystine and other diketopiperazines of cystine
    • Greenstein JP. Studies of multivalent amino acids and peptides. VIII. The synthesis of bisanhydro-L-cystinyl-L-cystine and other diketopiperazines of cystine. J. Biol. Chem. 1937; 118: 321-329.
    • (1937) J. Biol. Chem. , vol.118 , pp. 321-329
    • Greenstein, J.P.1
  • 51
    • 0013040537 scopus 로고
    • Opening of the ring of the thiolactone of homocysteine
    • du Vigneaud V, Patterson WI, Hunt M. Opening of the ring of the thiolactone of homocysteine. J. Biol. Chem. 1938; 126: 217-231.
    • (1938) J. Biol. Chem. , vol.126 , pp. 217-231
    • du Vigneaud, V.1    Patterson, W.I.2    Hunt, M.3
  • 52
    • 0013040345 scopus 로고
    • Studien ueber den Einfluss der an der Bildung von Aminosaeureestern beteiligten Alkoholgruppe auf die Geschwindigkeit der Bildung von 2,5-Dioxopiperazinen und die Entstehung von Guanidinoverbindungen bei der Einwirkung von Guanidin auf verschiedene Aminosaeureester
    • Abderhalden E, Suzuki S. Studien ueber den Einfluss der an der Bildung von Aminosaeureestern beteiligten Alkoholgruppe auf die Geschwindigkeit der Bildung von 2,5-Dioxopiperazinen und die Entstehung von Guanidinoverbindungen bei der Einwirkung von Guanidin auf verschiedene Aminosaeureester. Hoppe-Seyler's Z. Physiol. Chem. 1928; 176: 101-108.
    • (1928) Hoppe-Seyler's Z. Physiol. Chem. , vol.176 , pp. 101-108
    • Abderhalden, E.1    Suzuki, S.2
  • 54
    • 0013873081 scopus 로고
    • New methods in peptide synthesis. Protection of carboxyl group
    • Stelakatos GC, Paganou A, Zervas L. New methods in peptide synthesis. Part III. Protection of carboxyl group. J. Chem. Soc. C. 1966; 1191-1199.
    • (1966) J. Chem. Soc. C. , Issue.PART III , pp. 1191-1199
    • Stelakatos, G.C.1    Paganou, A.2    Zervas, L.3
  • 56
    • 0028940110 scopus 로고
    • Synthesis of large peptides in solution
    • Sakakibara S. Synthesis of large peptides in solution. Biopolymers Pept. Sci. 1995; 37: 17-28.
    • (1995) Biopolymers Pept. Sci. , vol.37 , pp. 17-28
    • Sakakibara, S.1
  • 58
    • 0025095466 scopus 로고
    • Rapid continuous peptide synthesis via FMOC amino acid chloride coupling and 4-(aminomethyl)piperidine deblocking
    • Beyermann M, Bienert M, Niedrich H, Carpino LA, Sadat-Aalaee D. Rapid continuous peptide synthesis via FMOC amino acid chloride coupling and 4-(aminomethyl)piperidine deblocking. J. Org. Chem. 1990; 55: 721-728.
    • (1990) J. Org. Chem. , vol.55 , pp. 721-728
    • Beyermann, M.1    Bienert, M.2    Niedrich, H.3    Carpino, L.A.4    Sadat-Aalaee, D.5
  • 59
    • 0016901368 scopus 로고
    • Amino acids and peptides. XXXIX. Synthesis of analogs of bradykinin with modifications in positions 1, 6, and 9
    • Pinker TG, Young GT, Elliott DF, Wade R. Amino acids and peptides. XXXIX. Synthesis of analogs of bradykinin with modifications in positions 1, 6, and 9. J. Chem. Soc. Perkin Trans. 1 1976; 220-228.
    • (1976) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 220-228
    • Pinker, T.G.1    Young, G.T.2    Elliott, D.F.3    Wade, R.4
  • 60
    • 0029874160 scopus 로고    scopus 로고
    • Synthesis of the marine sponge cycloheptapeptide stylopeptide 1
    • Pettit GR, Taylor SR. Synthesis of the marine sponge cycloheptapeptide stylopeptide 1. J. Org. Chem. 1996; 61: 2322-2325.
    • (1996) J. Org. Chem. , vol.61 , pp. 2322-2325
    • Pettit, G.R.1    Taylor, S.R.2
  • 61
    • 0023017976 scopus 로고
    • BOP-Cl mediated synthesis of the cyclosporine A 8-11 tetrapeptide fragment
    • Tung RD, Dhaon MK, Rich DH. BOP-Cl mediated synthesis of the cyclosporine A 8-11 tetrapeptide fragment. J. Org. Chem. 1986; 51: 3350-3354.
    • (1986) J. Org. Chem. , vol.51 , pp. 3350-3354
    • Tung, R.D.1    Dhaon, M.K.2    Rich, D.H.3
  • 62
    • 0028300132 scopus 로고
    • Solution synthesis of a dimeric pentapeptide: Diketopiperazine cyclisation of Glu-Asp dipeptide esters and Aspracemisation during segment condensation
    • Fischer PM, Solbakken M, Undheim K. Solution synthesis of a dimeric pentapeptide: diketopiperazine cyclisation of Glu-Asp dipeptide esters and Aspracemisation during segment condensation. Tetrahedron 1994; 50: 2277-2288.
    • (1994) Tetrahedron , vol.50 , pp. 2277-2288
    • Fischer, P.M.1    Solbakken, M.2    Undheim, K.3
  • 63
    • 0014820265 scopus 로고
    • Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid und 3-Hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazin
    • Koenig W, Geiger R. Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid und 3-Hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazin. Chem. Ber. 1970; 103: 2034-2040.
    • (1970) Chem. Ber. , vol.103 , pp. 2034-2040
    • Koenig, W.1    Geiger, R.2
  • 64
    • 0015267572 scopus 로고
    • Synthese von [2,7-Cystin]-Gramicidin S, einem kuenstlichen homodet-heterodet-bicyclischen Decapeptid
    • Ludescher U, Schwyzer R. Synthese von [2,7-Cystin]-Gramicidin S, einem kuenstlichen homodet-heterodet-bicyclischen Decapeptid. Helv. Chim. Acta 1972; 55: 2052-2060.
    • (1972) Helv. Chim. Acta , vol.55 , pp. 2052-2060
    • Ludescher, U.1    Schwyzer, R.2
  • 65
    • 0000160282 scopus 로고
    • 2-(2-Pyridyl-)ethyl esters. A new carboxyl protecting group in peptide synthesis
    • Kessler H, Becker G, Kogler H, Wolff M. 2-(2-Pyridyl-)ethyl esters. A new carboxyl protecting group in peptide synthesis. Tetrahedron Lett. 1984; 25: 3971-3974.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3971-3974
    • Kessler, H.1    Becker, G.2    Kogler, H.3    Wolff, M.4
  • 66
    • 0013040542 scopus 로고
    • 2-(Pyridyl)ethylester als sicherer und dennoch leicht abloesbarer polariphiler Carboxy-Schutz bei der Peptidsynthese
    • Kunz H, Kneip M. 2-(Pyridyl)ethylester als sicherer und dennoch leicht abloesbarer polariphiler Carboxy-Schutz bei der Peptidsynthese. Angew. Chem. 1984; 96: 702-704.
    • (1984) Angew Chem. , vol.96 , pp. 702-704
    • Kunz, H.1    Kneip, M.2
  • 67
    • 84943951457 scopus 로고
    • Ueber α-Halogenäther, VII. Reaktionen von Dichlormethyl-alkyl-aethern mit Aminosaeurederivaten
    • Poduska K, Gross H. Ueber α-Halogenäther, VII. Reaktionen von Dichlormethyl-alkyl-aethern mit Aminosaeurederivaten. Chem. Ber. 1961; 94: 527-537.
    • (1961) Chem. Ber. , vol.94 , pp. 527-537
    • Poduska, K.1    Gross, H.2
  • 68
    • 26144455058 scopus 로고
    • Poly-condensation of α-amino acid esters. II. Poly-condensation of alanine ethyl ester
    • Frankel M, Katchalski E. Poly-condensation of α-amino acid esters. II. Poly-condensation of alanine ethyl ester. J. Am. Chem. Soc. 1942; 64: 2268-2271.
    • (1942) J. Am. Chem. Soc. , vol.64 , pp. 2268-2271
    • Frankel, M.1    Katchalski, E.2
  • 69
    • 0020362292 scopus 로고
    • Studies on analgesic oligopeptides. II. Structure-activity relationship among thirty analogs of a cyclic dipeptide, cyclo(-Tyr-Arg-)
    • Sasaki Y, Akutsu Y, Matsui M, Suzuki K, Sakurada S, Sato T, Kisara K. Studies on analgesic oligopeptides. II. Structure-activity relationship among thirty analogs of a cyclic dipeptide, cyclo(-Tyr-Arg-). Chem. Pharm. Bull. 1982; 30: 4435-4443.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 4435-4443
    • Sasaki, Y.1    Akutsu, Y.2    Matsui, M.3    Suzuki, K.4    Sakurada, S.5    Sato, T.6    Kisara, K.7
  • 70
    • 0027724174 scopus 로고
    • Heterocyclic amino acids as synthons. Reactions with dicarbonyl compounds
    • Kolar P, Tisler M. Heterocyclic amino acids as synthons. Reactions with dicarbonyl compounds. J. Heterocycl. Chem. 1993; 30: 1253-1260.
    • (1993) J. Heterocycl. Chem. , vol.30 , pp. 1253-1260
    • Kolar, P.1    Tisler, M.2
  • 71
    • 0013038815 scopus 로고
    • UV photoelectron spectra of peptide unit model compounds: Methionyl-containing cyclic dipeptides
    • Ajo D, Granozzi G, Guantieri V, Tamburro AM. UV photoelectron spectra of peptide unit model compounds: methionyl-containing cyclic dipeptides. J. Mol. Struct. 1983; 96: 369-372.
    • (1983) J. Mol. Struct. , vol.96 , pp. 369-372
    • Ajo, D.1    Granozzi, G.2    Guantieri, V.3    Tamburro, A.M.4
  • 74
    • 0000555814 scopus 로고
    • Active esters in peptide synthesis
    • Academic Press: New York
    • Bodanszky M. Active esters in peptide synthesis. In The Peptides: Analysis, Synthesis, Biology. Academic Press: New York, 1979; 105-196.
    • (1979) The Peptides: Analysis, Synthesis, Biology , pp. 105-196
    • Bodanszky, M.1
  • 76
    • 0013086725 scopus 로고
    • Polypeptides. The self-condensation of the esters of some peptides of glycine and proline
    • Rydon HN, Smith PWG. Polypeptides. Part IV. The self-condensation of the esters of some peptides of glycine and proline. J. Chem. Soc. 1956; 3642-3650.
    • (1956) J. Chem. Soc. , Issue.PART IV , pp. 3642-3650
    • Rydon, H.N.1    Smith, P.W.G.2
  • 77
    • 0027532576 scopus 로고
    • Spontaneous degradation via diketopiperazine formation of peptides containing a tetrahydroisoquinoline-3-carboxylic acid residue in the 2-position of the peptide sequence
    • Marsden BJ, Nguyen TM-D, Schiller PW. Spontaneous degradation via diketopiperazine formation of peptides containing a tetrahydroisoquinoline-3-carboxylic acid residue in the 2-position of the peptide sequence. Int. J. Peptide Protein Res. 1993; 41: 313-316.
    • (1993) Int. J. Peptide Protein Res. , vol.41 , pp. 313-316
    • Marsden, B.J.1    Nguyen, T.M.-D.2    Schiller, P.W.3
  • 78
    • 0001151805 scopus 로고
    • TIPP opioid peptides: Development of extraordinarily potent and selective D antagonists and observation of astonishing structure-intrinsic activity relationships
    • ESCOM: Leiden
    • Schiller PW, Nguyen TM-D, Weltrowska G, Wilkes BC, Lemieux C, Chung NN. TIPP opioid peptides: development of extraordinarily potent and selective D antagonists and observation of astonishing structure-intrinsic activity relationships. In Peptides: Chemistry, Structure and Biology. ESCOM: Leiden, 1994; 483-486.
    • (1994) Peptides: Chemistry, Structure and Biology , pp. 483-486
    • Schiller, P.W.1    Nguyen, T.M.-D.2    Weltrowska, G.3    Wilkes, B.C.4    Lemieux, C.5    Chung, N.N.6
  • 79
    • 0028077859 scopus 로고
    • Spontaneous diketopiperazine formation via end-to-end cyclization of a nonactivated linear tripeptide: An unusual chemical reaction
    • Carpenter KA, Weltrowska G, Wilkes BC, Schmidt R, Schiller PW. Spontaneous diketopiperazine formation via end-to-end cyclization of a nonactivated linear tripeptide: an unusual chemical reaction. J. Am. Chem. Soc. 1994; 116: 8450-8458.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8450-8458
    • Carpenter, K.A.1    Weltrowska, G.2    Wilkes, B.C.3    Schmidt, R.4    Schiller, P.W.5
  • 80
    • 0023481924 scopus 로고
    • Diketopiperazine formation, hydrolysis, and epimerization of the new dipeptide angiotensin-converting enzyme inhibitor RS-10085
    • Gu L, Strickley RG. Diketopiperazine formation, hydrolysis, and epimerization of the new dipeptide angiotensin-converting enzyme inhibitor RS-10085. Pharm. Res. 1987; 4: 392-397.
    • (1987) Pharm. Res. , vol.4 , pp. 392-397
    • Gu, L.1    Strickley, R.G.2
  • 82
    • 0015326316 scopus 로고
    • Side-reactions arising on formation of cyclodipeptides in solid-phase peptide synthesis
    • Rothe M, Mazanek J. Side-reactions arising on formation of cyclodipeptides in solid-phase peptide synthesis. Angew. Chem. Int. Ed. Engl. 1972; 11: 293.
    • (1972) Angew Chem. Int. Ed. Engl. , vol.11 , pp. 293
    • Rothe, M.1    Mazanek, J.2
  • 83
    • 0002472980 scopus 로고
    • Formation of cyclic dipeptides and bi- and tricyclic products from linear tetrapeptides
    • Ann Arbor Science Publishers
    • Titlestad K. Formation of cyclic dipeptides and bi- and tricyclic products from linear tetrapeptides. In Chemistry and Biology of Peptides. Ann Arbor Science Publishers, 1972; 59-65.
    • (1972) Chemistry and Biology of Peptides , pp. 59-65
    • Titlestad, K.1
  • 84
    • 0015527159 scopus 로고
    • Failure sequence in solid-phase peptide synthesis due to the presence of an N-alkylamino acid
    • Khoshla MC, Smeby RR, Bumpus FM. Failure sequence in solid-phase peptide synthesis due to the presence of an N-alkylamino acid. J. Am. Chem. Soc. 1972; 94: 4721-4726.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 4721-4726
    • Khoshla, M.C.1    Smeby, R.R.2    Bumpus, F.M.3
  • 85
    • 4243615024 scopus 로고
    • Structure of N,N′-ditrityl-2,5-diketopiperazine and its 1 : 1 inclusion complex with methylene chloride
    • Goldberg I, Stein Z, Lin L-TW, Hart H. Structure of N,N′-ditrityl-2,5-diketopiperazine and its 1 : 1 inclusion complex with methylene chloride. Acta Cryst. 1985; C41: 1539-1543.
    • (1985) Acta Cryst. , vol.41 C , pp. 1539-1543
    • Goldberg, I.1    Stein, Z.2    Lin, L.-T.W.3    Hart, H.4
  • 86
    • 0001792085 scopus 로고
    • α-symmetrically disubstituted glycines: Useful building blocks in the design of conformationally restricted peptides
    • α-symmetrically disubstituted glycines: useful building blocks in the design of conformationally restricted peptides. Janssen Chim. Acta 1993; 11: 10-16.
    • (1993) Janssen Chim. Acta , vol.11 , pp. 10-16
    • Toniolo, C.1
  • 87
    • 0013086552 scopus 로고
    • Facile diketopiperazine formation from dipeptides containing α-aminoisobutyric acid. Conformational factors influencing cyclisation
    • Nagaraj R, Balaram P. Facile diketopiperazine formation from dipeptides containing α-aminoisobutyric acid. Conformational factors influencing cyclisation. Heterocycles 1977; 7: 885-890.
    • (1977) Heterocycles , vol.7 , pp. 885-890
    • Nagaraj, R.1    Balaram, P.2
  • 88
    • 0001390681 scopus 로고
    • Bi- and tricyclic products from tetra- and pentapeptides of α-methylalanine
    • Ali MY, Dale J, Titlestad K. Bi- and tricyclic products from tetra- and pentapeptides of α-methylalanine. Acta Chem. Scand. 1973; 27: 1509-1518.
    • (1973) Acta Chem. Scand. , vol.27 , pp. 1509-1518
    • Ali, M.Y.1    Dale, J.2    Titlestad, K.3
  • 89
    • 33947447039 scopus 로고
    • Esters of α-aminoisobutyric acid
    • Jacobson RA. Esters of α-aminoisobutyric acid. J. Am. Chem. Soc. 1946; 68: 2628-2630.
    • (1946) J. Am. Chem. Soc. , vol.68 , pp. 2628-2630
    • Jacobson, R.A.1
  • 90
    • 0000270788 scopus 로고
    • Sensitivity of polypeptide conformation to geometry. Theoretical conformational analysis of oligomers of α-aminoisobutyric acid
    • Paterson Y, Rumsey SM, Benedetti E, Nemethy G, Scheraga HA. Sensitivity of polypeptide conformation to geometry. Theoretical conformational analysis of oligomers of α-aminoisobutyric acid. J. Am. Chem. Soc. 1981; 103: 2947-2955.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 2947-2955
    • Paterson, Y.1    Rumsey, S.M.2    Benedetti, E.3    Nemethy, G.4    Scheraga, H.A.5
  • 91
    • 0013074536 scopus 로고
    • The utility of the four-dimensional Ramachandran map for the description of peptide conformations
    • Perczel A, Kajtar M, Marcoccia JF, Csizmadia IG. The utility of the four-dimensional Ramachandran map for the description of peptide conformations. J. Mol. Struct. 1991; 232: 291-319.
    • (1991) J. Mol. Struct. , vol.232 , pp. 291-319
    • Perczel, A.1    Kajtar, M.2    Marcoccia, J.F.3    Csizmadia, I.G.4
  • 92
    • 0019156518 scopus 로고
    • Bradykinin analogs containing α-aminoisobutyric acid (Aib)
    • Vavrek RJ, Stewart JM. Bradykinin analogs containing α-aminoisobutyric acid (Aib). Peptides 1980; 1: 231-235.
    • (1980) Peptides , vol.1 , pp. 231-235
    • Vavrek, R.J.1    Stewart, J.M.2
  • 93
    • 37049062259 scopus 로고
    • Peptides. XVII. Synthesis of peptides and polymers of some sterically hindered amino acids via oxazolone intermediates
    • Jones DS, Kenner GW, Preston J, Sheppard RC. Peptides. XVII. Synthesis of peptides and polymers of some sterically hindered amino acids via oxazolone intermediates. J. Chem. Soc. 1965; 6227-6239.
    • (1965) J. Chem. Soc. , pp. 6227-6239
    • Jones, D.S.1    Kenner, G.W.2    Preston, J.3    Sheppard, R.C.4
  • 94
    • 0013811553 scopus 로고
    • Peptides. XIX. Isomerization of oxazolones derived from tripeptides
    • Jones DS, Kenner GW, Preston J, Sheppard RC. Peptides. XIX. Isomerization of oxazolones derived from tripeptides. Tetrahedron 1965; 21: 3209-3218.
    • (1965) Tetrahedron , vol.21 , pp. 3209-3218
    • Jones, D.S.1    Kenner, G.W.2    Preston, J.3    Sheppard, R.C.4
  • 95
    • 0014977099 scopus 로고
    • Cystinpeptide aus (S-Acetamidomethyl-cystein)-peptiden durch Oxydation mit Jod: Die Synthese von cyclo-L-Cystin
    • Kamber B. Cystinpeptide aus (S-Acetamidomethyl-cystein)-peptiden durch Oxydation mit Jod: Die Synthese von cyclo-L-Cystin. Helv. Chim. Acta 1971; 54: 927-930.
    • (1971) Helv. Chim. Acta , vol.54 , pp. 927-930
    • Kamber, B.1
  • 96
    • 84987310078 scopus 로고
    • Peptide, LXXIX. Merrifield-Synthese symmetrischer Cystinpeptide
    • Lunkenheimer W, Zahn H. Peptide, LXXIX. Merrifield-Synthese symmetrischer Cystinpeptide. Liebigs Ann. Chem. 1970; 740: 1-17.
    • (1970) Liebigs Ann. Chem. , vol.740 , pp. 1-17
    • Lunkenheimer, W.1    Zahn, H.2
  • 97
    • 0027310803 scopus 로고
    • Formation of pyroglutamylglutamine (or asparagine) diketopiperazine in 'non-classical' conditions: A side reaction in peptide synthesis
    • Mazurov AA, Andronati SA, Korotenko TI, Gorbatyuk VY, Shapiro YE. Formation of pyroglutamylglutamine (or asparagine) diketopiperazine in 'non-classical' conditions: a side reaction in peptide synthesis. Int. J. Peptide Protein Res. 1993: 42: 14-19.
    • (1993) Int. J. Peptide Protein Res. , vol.42 , pp. 14-19
    • Mazurov, A.A.1    Andronati, S.A.2    Korotenko, T.I.3    Gorbatyuk, V.Y.4    Shapiro, Y.E.5
  • 98
    • 0019501918 scopus 로고
    • Synthesis of thyrotropin-releasing hormone analogues with selective central nervous systems effects
    • Nutt RF, Holly FW, Homnick C, Hirschmann R, Veber DF. Synthesis of thyrotropin-releasing hormone analogues with selective central nervous systems effects. J. Med. Chem. 1981; 24: 692-698.
    • (1981) J. Med. Chem. , vol.24 , pp. 692-698
    • Nutt, R.F.1    Holly, F.W.2    Homnick, C.3    Hirschmann, R.4    Veber, D.F.5
  • 99
    • 0017318380 scopus 로고
    • Attempted synthesis of 2-methylalanyl-L-prolyl-L-tryptophan. An unexpected result
    • Gerig JT, McLeod RS. Attempted synthesis of 2-methylalanyl-L-prolyl-L-tryptophan. An unexpected result. J. Org. Chem. 1976; 41: 1653-1655.
    • (1976) J. Org. Chem. , vol.41 , pp. 1653-1655
    • Gerig, J.T.1    McLeod, R.S.2
  • 100
    • 0000871688 scopus 로고
    • A novel peptide cleavage reaction
    • Mazur RH, Schlatter JM. A novel peptide cleavage reaction. J. Org. Chem. 1963; 28: 1025-1029.
    • (1963) J. Org. Chem. , vol.28 , pp. 1025-1029
    • Mazur, R.H.1    Schlatter, J.M.2
  • 101
    • 0000833934 scopus 로고
    • Peptide decomposition in the neutral pH region via the formation of diketopiperazines
    • Steinberg SM, Bada JL. Peptide decomposition in the neutral pH region via the formation of diketopiperazines. J. Org. Chem. 1983; 48: 2295-2298.
    • (1983) J. Org. Chem. , vol.48 , pp. 2295-2298
    • Steinberg, S.M.1    Bada, J.L.2
  • 104
    • 0013768663 scopus 로고
    • Stereospecific cyclolization of N-(α-hydroxyacyl)-phenylalaninyl-proline lactams
    • Ott H, Frey AJ, Hofmann A. Stereospecific cyclolization of N-(α-hydroxyacyl)-phenylalaninyl-proline lactams. Tetrahedron 1963; 19: 1675-1684.
    • (1963) Tetrahedron , vol.19 , pp. 1675-1684
    • Ott, H.1    Frey, A.J.2    Hofmann, A.3
  • 105
    • 0000859279 scopus 로고
    • First-order rate constants for the racemization of each component in a mixture of isomeric dipeptides and their diketopiperazines
    • Smith GG, Baum R. First-order rate constants for the racemization of each component in a mixture of isomeric dipeptides and their diketopiperazines. J. Org. Chem. 1987; 52: 2248-2255.
    • (1987) J. Org. Chem. , vol.52 , pp. 2248-2255
    • Smith, G.G.1    Baum, R.2
  • 106
    • 0000799827 scopus 로고
    • Aspartame decomposition and epimerization in the diketopiperazine and dipeptide products as a function of pH and temperature
    • Gaines SM, Bada JL. Aspartame decomposition and epimerization in the diketopiperazine and dipeptide products as a function of pH and temperature. J. Org. Chem. 1988; 53: 2757-2764.
    • (1988) J. Org. Chem. , vol.53 , pp. 2757-2764
    • Gaines, S.M.1    Bada, J.L.2
  • 109
    • 0026062041 scopus 로고
    • Ultraviolet resonance Raman studies of trans and cis peptides: Photochemical consequences of the twisted π* excited state
    • Song S, Asher SA, Krimm S, Shaw KD. Ultraviolet resonance Raman studies of trans and cis peptides: photochemical consequences of the twisted π* excited state. J. Am. Chem. Soc. 1991; 113: 1155-1163.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1155-1163
    • Song, S.1    Asher, S.A.2    Krimm, S.3    Shaw, K.D.4
  • 110
    • 0000580786 scopus 로고
    • Conformations of cyclic dipeptides. Structure of cyclo-glycyl-L-tyrosyl (L-3-(4-hydroxybenzyl)-2,5-piperazinedione)
    • Webb LE, Lin C-F. Conformations of cyclic dipeptides. Structure of cyclo-glycyl-L-tyrosyl (L-3-(4-hydroxybenzyl)-2,5-piperazinedione). J. Am. Chem. Soc. 1971; 93: 3818-3819.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 3818-3819
    • Webb, L.E.1    Lin, C.-F.2
  • 111
    • 0000146739 scopus 로고
    • Crystal structure of diketopiperazine
    • Corey RB. Crystal structure of diketopiperazine. J. Am. Chem. Soc. 1938; 60: 1598-1604.
    • (1938) J. Am. Chem. Soc. , vol.60 , pp. 1598-1604
    • Corey, R.B.1
  • 112
    • 0013132029 scopus 로고
    • Optical rotatory properties of diketopiperazines
    • Balasubramanian D, Wetlaufer DB. Optical rotatory properties of diketopiperazines. J. Am. Chem. Soc. 1966; 88: 3449-3450.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 3449-3450
    • Balasubramanian, D.1    Wetlaufer, D.B.2
  • 113
    • 84984261963 scopus 로고
    • Flexibility of supposed 'rigid' molecules: Substituted 2,5-piperazinediones (diketopiperazines)
    • Benedetti E, Corradini P, Goodman M, Pedone C. Flexibility of supposed 'rigid' molecules: substituted 2,5-piperazinediones (diketopiperazines). Proc. Natl. Acad. Sci. USA 1969; 62: 650-652.
    • (1969) Proc. Natl. Acad. Sci. USA , vol.62 , pp. 650-652
    • Benedetti, E.1    Corradini, P.2    Goodman, M.3    Pedone, C.4
  • 114
    • 0013038994 scopus 로고
    • Optical rotatory power in the ground state and electronically excited state of diketopiperazines containing aromatic side chains
    • Schlessinger J, Gafni A, Steinberg IZ. Optical rotatory power in the ground state and electronically excited state of diketopiperazines containing aromatic side chains. J. Am. Chem. Soc. 1974; 96: 7396-7400.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 7396-7400
    • Schlessinger, J.1    Gafni, A.2    Steinberg, I.Z.3
  • 115
    • 0014672233 scopus 로고
    • Conformations of cyclic peptides. II. Side-chain conformation and ring shape in cyclic dipeptides
    • Kopple KD, Ohnishi M. Conformations of cyclic peptides. II. Side-chain conformation and ring shape in cyclic dipeptides. J. Am. Chem. Soc. 1969; 91: 962-970.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 962-970
    • Kopple, K.D.1    Ohnishi, M.2
  • 116
    • 0001255218 scopus 로고
    • Spin-forbidden excitation transfer and heavy-atom induced intersystem crossing in linear and cyclic peptides
    • Basu G, Kubasik M, Anglos D, Kuki A. Spin-forbidden excitation transfer and heavy-atom induced intersystem crossing in linear and cyclic peptides. J. Phys. Chem. 1993; 97: 3956-3967.
    • (1993) J. Phys. Chem. , vol.97 , pp. 3956-3967
    • Basu, G.1    Kubasik, M.2    Anglos, D.3    Kuki, A.4
  • 117
    • 37049090519 scopus 로고
    • NMR assignments, conformation, and absolute configuration of ditryptophenaline and model dioxopiperazines
    • Maes CM, Potgieter M, Steyn PS. NMR assignments, conformation, and absolute configuration of ditryptophenaline and model dioxopiperazines. J. Chem. Soc. Perkin Trans. 1 1986; 861-866.
    • (1986) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 861-866
    • Maes, C.M.1    Potgieter, M.2    Steyn, P.S.3
  • 120
    • 84943117665 scopus 로고
    • Die Konformation des Prolin-Ringes in Diketopiperazin-Systemen
    • Siemion IZ. Die Konformation des Prolin-Ringes in Diketopiperazin-Systemen. Liebigs Ann. Chem. 1971; 748: 88-95.
    • (1971) Liebigs Ann. Chem. , vol.748 , pp. 88-95
    • Siemion, I.Z.1
  • 121
    • 0025119456 scopus 로고
    • Multi-pin peptide synthesis strategy for T cell determinant analysis
    • Maeji NJ, Bray AM, Geysen HM. Multi-pin peptide synthesis strategy for T cell determinant analysis. J. Immunol. Methods 1990; 134: 23-33.
    • (1990) J. Immunol. Methods , vol.134 , pp. 23-33
    • Maeji, N.J.1    Bray, A.M.2    Geysen, H.M.3
  • 122
    • 0001689141 scopus 로고
    • Direct cleavage of peptides from a solid support into aqueous buffer. Application in simultaneous multiple peptide synthesis
    • Bray AM, Maeji NJ, Valerio RM, Campbell RA, Geysen HM. Direct cleavage of peptides from a solid support into aqueous buffer. Application in simultaneous multiple peptide synthesis. J. Org. Chem. 1991; 56: 6659-6666.
    • (1991) J. Org. Chem. , vol.56 , pp. 6659-6666
    • Bray, A.M.1    Maeji, N.J.2    Valerio, R.M.3    Campbell, R.A.4    Geysen, H.M.5
  • 125
    • 0027214153 scopus 로고
    • Multistep deprotection for peptide chemistry
    • Patek M. Multistep deprotection for peptide chemistry. Int. J. Peptide Protein Res. 1993; 42: 97-117.
    • (1993) Int. J. Peptide Protein Res. , vol.42 , pp. 97-117
    • Patek, M.1
  • 126
    • 0001275595 scopus 로고
    • A comparison of acid labile linkage agents for the synthesis of peptide C-terminal amides
    • Bernatowicz MS, Daniels SB, Koester H. A comparison of acid labile linkage agents for the synthesis of peptide C-terminal amides. Tetrahedron Lett. 1989; 30: 4645-4648.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4645-4648
    • Bernatowicz, M.S.1    Daniels, S.B.2    Koester, H.3
  • 127
    • 0026532674 scopus 로고
    • Preparation of protected peptide amides using Fmoc chemical protocol. Comparison of resins for solid phase synthesis
    • Story SC, Aldrich JV. Preparation of protected peptide amides using Fmoc chemical protocol. Comparison of resins for solid phase synthesis. Int. J. Peptide Protein Res. 1992; 39: 87-92.
    • (1992) Int. J. Peptide Protein Res. , vol.39 , pp. 87-92
    • Story, S.C.1    Aldrich, J.V.2
  • 128
    • 37049106853 scopus 로고
    • α-fluorenylmethoxycarbonylamino-acids on polyamide supports. Synthesis of substance P and acyl carrier protein 65-74 decapeptide
    • α-fluorenylmethoxycarbonylamino-acids on polyamide supports. Synthesis of substance P and acyl carrier protein 65-74 decapeptide. J. Chem. Soc. Perkin Trans. 1 1981; 538-546.
    • (1981) J. Chem. Soc. Perkin Trans. , vol.1 , Issue.PART 2 , pp. 538-546
    • Atherton, E.1    Logan, C.J.2    Sheppard, R.C.3
  • 130
    • 0028220676 scopus 로고
    • The role of solid-phase fragment condensation (SPFC) in peptide synthesis
    • Benz H. The role of solid-phase fragment condensation (SPFC) in peptide synthesis. Synthesis 1994; 337-358.
    • (1994) Synthesis , pp. 337-358
    • Benz, H.1
  • 131
    • 0025232814 scopus 로고
    • Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids
    • Fields GB, Noble RL. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Peptide Protein Res. 1990; 35: 161-214.
    • (1990) Int. J. Peptide Protein Res. , vol.35 , pp. 161-214
    • Fields, G.B.1    Noble, R.L.2
  • 133
    • 20744456789 scopus 로고
    • Solid phase peptide synthesis. I. The synthesis of a tetrapeptide
    • Merrifield RB. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963; 85: 2145-2154.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2145-2154
    • Merrifield, R.B.1
  • 134
    • 0001293516 scopus 로고
    • Diketopiperazine formation in acetamido- and nitrobenzamido-bridged polymeric supports
    • Giralt E, Eritja R, Pedroso E. Diketopiperazine formation in acetamido- and nitrobenzamido-bridged polymeric supports. Tetrahedron Lett. 1981; 22: 3779-3782.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3779-3782
    • Giralt, E.1    Eritja, R.2    Pedroso, E.3
  • 135
    • 0002258830 scopus 로고
    • Solid-phase synthesis of peptides with the highly acid-sensitive HMPB linker
    • ESCOM: Leiden
    • Floersheimer A, Riniker B. Solid-phase synthesis of peptides with the highly acid-sensitive HMPB linker. Peptides 1990. ESCOM: Leiden, 1991; 131-133.
    • (1991) Peptides 1990 , pp. 131-133
    • Floersheimer, A.1    Riniker, B.2
  • 136
    • 45549111520 scopus 로고
    • Peptide synthesis by a combination of solid-phase and solution methods. I. A new very acid-labile anchor for the solid phase synthesis of fully protected fragments
    • Mergler M, Tanner R, Gosteli J, Grogg P. Peptide synthesis by a combination of solid-phase and solution methods. I. A new very acid-labile anchor for the solid phase synthesis of fully protected fragments. Tetrahedron Lett. 1988; 29: 4005-4008.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4005-4008
    • Mergler, M.1    Tanner, R.2    Gosteli, J.3    Grogg, P.4
  • 137
    • 0020214402 scopus 로고
    • Acid-labile resin linkage agents for use in solid phase peptide synthesis
    • Sheppard RC, Williams BJ. Acid-labile resin linkage agents for use in solid phase peptide synthesis. Int. J. Peptide Protein Res. 1982; 20: 451-454.
    • (1982) Int. J. Peptide Protein Res. , vol.20 , pp. 451-454
    • Sheppard, R.C.1    Williams, B.J.2
  • 138
    • 0015931593 scopus 로고
    • p-Alkoxybenzyl alcohol resin and p-alkoxybenzyloxycarbonylhydrazide resin for solid phase synthesis of protected peptide fragments
    • Wang S-S. p-Alkoxybenzyl alcohol resin and p-alkoxybenzyloxycarbonylhydrazide resin for solid phase synthesis of protected peptide fragments. J. Am. Chem. Soc. 1973; 95: 1328-1333.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 1328-1333
    • Wang, S.-S.1
  • 139
    • 37049077100 scopus 로고
    • Fmoc-based solid-phase peptide synthesis using a new t-alcohol type 4-(1′, 1′-dimethyl- 1′-hydroxypropyl)phenoxyacetyl handle (DHPP)-resin
    • Akaji K, Kiso Y, Carpino LA. Fmoc-based solid-phase peptide synthesis using a new t-alcohol type 4-(1′, 1′-dimethyl- 1′-hydroxypropyl)phenoxyacetyl handle (DHPP)-resin. J. Chem. Soc. Chem. Commun. 1990; 584-586.
    • (1990) J. Chem. Soc. Chem. Commun. , pp. 584-586
    • Akaji, K.1    Kiso, Y.2    Carpino, L.A.3
  • 140
    • 0001649196 scopus 로고
    • Esterification of N-protected α-amino acids with alcohol/carbodiimide/4-(dimethylamino)-pyridine. Racemization of aspartic and glutamic acid derivatives
    • Dhaon MK, Olsen RK, Ramasamy K. Esterification of N-protected α-amino acids with alcohol/carbodiimide/4-(dimethylamino)-pyridine. Racemization of aspartic and glutamic acid derivatives. J. Org. Chem. 1982; 47: 1962-1965.
    • (1982) J. Org. Chem. , vol.47 , pp. 1962-1965
    • Dhaon, M.K.1    Olsen, R.K.2    Ramasamy, K.3
  • 142
    • 0000609990 scopus 로고
    • The liquid phase method for peptide synthesis
    • Academic Press: New York
    • Mutter M, Bayer E. The liquid phase method for peptide synthesis. In The Peptides. Academic Press: New York, 1979; 285-332.
    • (1979) The Peptides , pp. 285-332
    • Mutter, M.1    Bayer, E.2
  • 144
    • 0000785097 scopus 로고
    • Use of polymers as protecting groups in organic synthesis. III. Selective functionalization of polyhydroxy alcohols
    • Frechet JMJ, Nuyens LJ. Use of polymers as protecting groups in organic synthesis. III. Selective functionalization of polyhydroxy alcohols. Can. J. Chem. 1976; 54: 926-934.
    • (1976) Can. J. Chem. , vol.54 , pp. 926-934
    • Frechet, J.M.J.1    Nuyens, L.J.2
  • 145
    • 0025767755 scopus 로고
    • 2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage
    • Barlos K, Chatzi O, Gatos D, Stavropoulos G. 2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage. Int. J. Peptide Protein Res. 1991; 37: 513-520.
    • (1991) Int. J. Peptide Protein Res. , vol.37 , pp. 513-520
    • Barlos, K.1    Chatzi, O.2    Gatos, D.3    Stavropoulos, G.4
  • 147
    • 0013039513 scopus 로고
    • Prediction and prevention of peptide conformations during synthesis
    • ESCOM: Leiden
    • Rapp WE, Bayer E. Prediction and prevention of peptide conformations during synthesis. In Peptides: Chemistry, Structure and Biology. ESCOM: Leiden, 1994; 40-43.
    • (1994) Peptides: Chemistry, Structure and Biology , pp. 40-43
    • Rapp, W.E.1    Bayer, E.2
  • 148
    • 37049074206 scopus 로고
    • A new reagent for the cleavage of fully protected peptides synthesised on 2-chlorotrityl chloride resin
    • Bollhagen R, Schmiedberger M, Barlos K, Grell E. A new reagent for the cleavage of fully protected peptides synthesised on 2-chlorotrityl chloride resin. J. Chem. Soc. Chem. Commun. 1994; 2559-2560.
    • (1994) J. Chem. Soc. Chem. Commun. , pp. 2559-2560
    • Bollhagen, R.1    Schmiedberger, M.2    Barlos, K.3    Grell, E.4
  • 149
    • 84871534868 scopus 로고
    • Solid phase syntheses (SPPS) of C-terminal proline peptides using an anchor system suppressing diketopiperazine (DKP) formation
    • Peptides, Proteins and Nucleic Acids. Biological and Biomedical Applications. Mayflower Worldwide: Birmingham
    • Gruebler G, Zimmermann H, Echner H, Stoeva S, Bernardi E, Pourrias B, Voelter W. Solid phase syntheses (SPPS) of C-terminal proline peptides using an anchor system suppressing diketopiperazine (DKP) formation. In Innovation and Perspective in Solid Phase Synthesis. Peptides, Proteins and Nucleic Acids. Biological and Biomedical Applications. Mayflower Worldwide: Birmingham, 1994; 517-520.
    • (1994) Innovation and Perspective in Solid Phase Synthesis , pp. 517-520
    • Gruebler, G.1    Zimmermann, H.2    Echner, H.3    Stoeva, S.4    Bernardi, E.5    Pourrias, B.6    Voelter, W.7
  • 150
    • 0001629148 scopus 로고
    • A new fluoridolysable anchoring linkage for orthogonal solid-phase peptide synthesis: Preparation and properties of the N-(3 or 4)-[[[(4-hydroxymethyl)-phenoxy-t-butylphenyl]silyl]phenyl]-pentanedioic acid, monoamide (PBS) handle
    • Mullen DG, Barany G. A new fluoridolysable anchoring linkage for orthogonal solid-phase peptide synthesis: preparation and properties of the N-(3 or 4)-[[[(4-hydroxymethyl)-phenoxy-t-butylphenyl]silyl]phenyl]-pentanedioic acid, monoamide (PBS) handle. Tetrahedron Lett. 1987; 28: 491-494.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 491-494
    • Mullen, D.G.1    Barany, G.2
  • 151
    • 0000905921 scopus 로고
    • Solid phase peptide synthesis: Fluoride ion release of peptide from the resin
    • Ramage R, Barron CA, Bielecki S, Thomas DW. Solid phase peptide synthesis: fluoride ion release of peptide from the resin. Tetrahedron Lett. 1987; 28: 4105-4108.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4105-4108
    • Ramage, R.1    Barron, C.A.2    Bielecki, S.3    Thomas, D.W.4
  • 152
    • 0018133234 scopus 로고
    • Synthesis and biological activity of two disulphide bond isomers of human insulin: [A7-A11,A6-B7-cystine]- and [A6-A7,A11-B7- cystine]insulin (human)
    • Sieber P, Eisler K, Kamber B, Riniker B, Rittel W, Maerki F, de Gasparo M. Synthesis and biological activity of two disulphide bond isomers of human insulin: [A7-A11,A6-B7-cystine]- and [A6-A7,A11-B7- cystine]insulin (human). Hoppe-Seyler's Z. Physiol. Chem. 1978; 359: 113-123.
    • (1978) Hoppe-Seyler's Z. Physiol. Chem. , vol.359 , pp. 113-123
    • Sieber, P.1    Eisler, K.2    Kamber, B.3    Riniker, B.4    Rittel, W.5    Maerki, F.6    de Gasparo, M.7
  • 153
    • 0001109169 scopus 로고
    • A novel and versatile silicon-derived linkage agent, 4-[1-hydroxy-2-(trimethylsilyl)ethyl]-benzoic acid, compatible with the Fmoc/t-Bu strategy for solid-phase synthesis of C-terminal peptide acids
    • Chao H-G, Bernatowicz MS, Reiss PD, Klimas CE, Matsueda GR. A novel and versatile silicon-derived linkage agent, 4-[1-hydroxy-2-(trimethylsilyl)ethyl]-benzoic acid, compatible with the Fmoc/t-Bu strategy for solid-phase synthesis of C-terminal peptide acids. J. Am. Chem. Soc. 1994; 116: 1746-1752.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1746-1752
    • Chao, H.-G.1    Bernatowicz, M.S.2    Reiss, P.D.3    Klimas, C.E.4    Matsueda, G.R.5
  • 154
    • 0037126838 scopus 로고    scopus 로고
    • The (2-phenyl-2-trimethylsilyl)-ethyl(PTMSEL) linker - A novel linker for the solid-phase synthesis of protected peptides and glycopeptides cleavable with fluoride
    • Wagner M, Kunz H. The (2-phenyl-2-trimethylsilyl)-ethyl(PTMSEL) linker - a novel linker for the solid-phase synthesis of protected peptides and glycopeptides cleavable with fluoride. Angew. Chem. Int. Ed. 2002; 41: 317-321.
    • (2002) Angew Chem. Int. Ed. , vol.41 , pp. 317-321
    • Wagner, M.1    Kunz, H.2
  • 155
    • 0001294786 scopus 로고
    • Convergent solid phase peptide synthesis. II. Synthesis of the 1-6 apamin protected segment on a NBB-resin. Synthesis of apamin
    • Giralt E, Albericio F, Pedroso E, Granier C, van Rietschoten J. Convergent solid phase peptide synthesis. II. Synthesis of the 1-6 apamin protected segment on a NBB-resin. Synthesis of apamin. Tetrahedron 1982; 38: 1193-1201.
    • (1982) Tetrahedron , vol.38 , pp. 1193-1201
    • Giralt, E.1    Albericio, F.2    Pedroso, E.3    Granier, C.4    van Rietschoten, J.5
  • 156
    • 0025932811 scopus 로고
    • Convergent solid-phase peptide synthesis. X. Synthesis and purification of protected peptide fragments using the photolabile Nbb-resin
    • Lloyd-Williams P, Gairi M, Albericio, F, Giralt E. Convergent solid-phase peptide synthesis. X. Synthesis and purification of protected peptide fragments using the photolabile Nbb-resin. Tetrahedron 1991; 47: 9867-9880.
    • (1991) Tetrahedron , vol.47 , pp. 9867-9880
    • Lloyd-Williams, P.1    Gairi, M.2    Albericio, F.3    Giralt, E.4
  • 157
    • 0013087619 scopus 로고
    • Solid-phase synthesis using a new polyacrylic resin. Synthesis of the fragment 14-21 of the amino acid sequence of histone H4
    • Calas B, Mery J, Parello J, Cave A. Solid-phase synthesis using a new polyacrylic resin. Synthesis of the fragment 14-21 of the amino acid sequence of histone H4. Tetrahedron 1985; 41: 5331-5339.
    • (1985) Tetrahedron , vol.41 , pp. 5331-5339
    • Calas, B.1    Mery, J.2    Parello, J.3    Cave, A.4
  • 158
    • 84913056807 scopus 로고
    • Towards anchoring groups allowing the use of aqueous media in solid phase peptide synthesis
    • Escom Science Publishers B.V.: Leiden
    • David M-L, Sola R, Pascal R. Towards anchoring groups allowing the use of aqueous media in solid phase peptide synthesis. In Peptides 1992. Escom Science Publishers B.V.: Leiden, 1993; 271-272.
    • (1993) Peptides 1992 , pp. 271-272
    • David, M.-L.1    Sola, R.2    Pascal, R.3
  • 160
    • 0025011819 scopus 로고
    • Synthesis of tryocidine A: Use of oxime resin for peptide chain assembly and cyclization
    • Oesapay G, Profit A, Taylor JW. Synthesis of tryocidine A: use of oxime resin for peptide chain assembly and cyclization. Tetrahedron Lett. 1990; 31: 6121-6124.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6121-6124
    • Oesapay, G.1    Profit, A.2    Taylor, J.W.3
  • 161
    • 33751500445 scopus 로고
    • Evaluation of the oxime resin based segment synthesis-condensation approach using RNase T1 as a model synthetic target
    • Sasaki T, Findeis MA, Kaiser ET. Evaluation of the oxime resin based segment synthesis-condensation approach using RNase T1 as a model synthetic target. J. Org. Chem. 1991; 56: 3159-3168.
    • (1991) J. Org. Chem. , vol.56 , pp. 3159-3168
    • Sasaki, T.1    Findeis, M.A.2    Kaiser, E.T.3
  • 162
    • 0001367609 scopus 로고
    • Synthesis of the 60 amino acid homeo domain and smaller fragments of the Drosophila gene regulatory protein Antennapedia by a segment synthesis-condensation approach
    • Mihara H, Chmielewski JA, Kaiser ET. Synthesis of the 60 amino acid homeo domain and smaller fragments of the Drosophila gene regulatory protein Antennapedia by a segment synthesis-condensation approach. J. Org. Chem. 1993; 58: 2209-2215.
    • (1993) J. Org. Chem. , vol.58 , pp. 2209-2215
    • Mihara, H.1    Chmielewski, J.A.2    Kaiser, E.T.3
  • 163
    • 0000441670 scopus 로고
    • Selective cleavage of protected amino acids and peptides from oxacyl resins by an 18-Crown-6 complex of potassium cyanide
    • Tam JP, Cunningham-Rundles WF, Erickson BW, Merrifield RB. Selective cleavage of protected amino acids and peptides from oxacyl resins by an 18-Crown-6 complex of potassium cyanide. Tetrahedron Lett. 1977; 4001-4004.
    • (1977) Tetrahedron Lett. , pp. 4001-4004
    • Tam, J.P.1    Cunningham-Rundles, W.F.2    Erickson, B.W.3    Merrifield, R.B.4
  • 164
    • 0024118219 scopus 로고
    • Noninvasive continuous monitoring of solid-phase peptide synthesis by acid-base indicator
    • Krchnak V, Vagner J, Lebl M. Noninvasive continuous monitoring of solid-phase peptide synthesis by acid-base indicator. Int. J. Peptide Protein Res. 1988; 32: 415-416.
    • (1988) Int. J. Peptide Protein Res. , vol.32 , pp. 415-416
    • Krchnak, V.1    Vagner, J.2    Lebl, M.3
  • 165
    • 0025822052 scopus 로고
    • Conductance measurements in solid phase peptide synthesis. I. Monitoring coupling and deprotection in Fmoc chemistry
    • McFerran NV, Walker B, McGurk CD, Scott FC. Conductance measurements in solid phase peptide synthesis. I. Monitoring coupling and deprotection in Fmoc chemistry. Int. J. Peptide Protein Res. 1991; 37: 382-387.
    • (1991) Int. J. Peptide Protein Res. , vol.37 , pp. 382-387
    • McFerran, N.V.1    Walker, B.2    McGurk, C.D.3    Scott, F.C.4
  • 166
    • 0029318692 scopus 로고
    • Multiple peptide synthesis
    • Fox JE. Multiple peptide synthesis. Mol. Biotechnol. 1995; 3: 249-258.
    • (1995) Mol. Biotechnol. , vol.3 , pp. 249-258
    • Fox, J.E.1
  • 167
    • 0021239054 scopus 로고
    • Synthesis of thyrotropin-releasing hormone analogues. 1. Complete dissociation of central nervous system effects from thyrotropin-releasing activity
    • Szirtes T, Kisfaludy L, Palosi E, Szporny L. Synthesis of thyrotropin-releasing hormone analogues. 1. Complete dissociation of central nervous system effects from thyrotropin-releasing activity. J. Med. Chem. 1984; 27: 741-745.
    • (1984) J. Med. Chem. , vol.27 , pp. 741-745
    • Szirtes, T.1    Kisfaludy, L.2    Palosi, E.3    Szporny, L.4
  • 168
    • 0013040001 scopus 로고
    • Reduction of diketopiperazine formation in Fmoc-peptide synthesis
    • Horwood: London
    • Cammish LE. Reduction of diketopiperazine formation in Fmoc-peptide synthesis. In Polypept. Protein Drugs. Horwood: London, 1991; 265-269.
    • (1991) Polypept. Protein Drugs , pp. 265-269
    • Cammish, L.E.1
  • 169
    • 85008894386 scopus 로고
    • Diketopiperazine formation in solid phase peptide synthesis using p-alkoxybenzyl ester resins and Fmoc-amino acids
    • Pedroso E, Grandas A, de las Heras X, Eritja R, Giralt E. Diketopiperazine formation in solid phase peptide synthesis using p-alkoxybenzyl ester resins and Fmoc-amino acids. Tetrahedron Lett. 1986; 27: 743-746.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 743-746
    • Pedroso, E.1    Grandas, A.2    de las Heras, X.3    Eritja, R.4    Giralt, E.5
  • 170
    • 0014436281 scopus 로고
    • Selective acidolytic cleavage of aralkyloxycarbonyl amino-protecting groups
    • Sieber P, Iselin BM. Selective acidolytic cleavage of aralkyloxycarbonyl amino-protecting groups. Helv. Chim. Acta 1968; 51: 614-622.
    • (1968) Helv. Chim. Acta , vol.51 , pp. 614-622
    • Sieber, P.1    Iselin, B.M.2
  • 171
    • 0001117875 scopus 로고
    • Removal of 9-fluorenylmethyloxycarbonyl (Fmoc) group with tetrabutylammonium fluoride
    • Ueki M, Amemiya M. Removal of 9-fluorenylmethyloxycarbonyl (Fmoc) group with tetrabutylammonium fluoride. Tetrahedron Lett. 1987; 28: 6617-6620.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6617-6620
    • Ueki, M.1    Amemiya, M.2
  • 172
    • 84944509053 scopus 로고
    • 13C NMR investigations of an inhibitor of hematopoietic stem cell proliferation Ac-Ser-Asp- Lys-Pro-OH
    • 13C NMR investigations of an inhibitor of hematopoietic stem cell proliferation Ac-Ser-Asp- Lys-Pro-OH. Z. Naturforsch. 1992; 47b: 1324-1332.
    • (1992) Z. Naturforsch. , vol.47 b , pp. 1324-1332
    • Freund, J.1    Kapurniotu, A.2    Holak, T.A.3    Lenfant, M.4    Voelter, W.5
  • 173
    • 0013086385 scopus 로고
    • Optimized SPPS of the new stem cell proliferation inhibiting factor Ac-SDKP and derivatives
    • Intercept: Andover, UK
    • Kapurniotu A, Ungermann C, Voelter W. Optimized SPPS of the new stem cell proliferation inhibiting factor Ac-SDKP and derivatives. In Innovation Perspect. Solid Phase Synthesis. Intercept: Andover, UK, 1992; 319-329.
    • (1992) Innovation Perspect. Solid Phase Synthesis , pp. 319-329
    • Kapurniotu, A.1    Ungermann, C.2    Voelter, W.3
  • 174
    • 0026151057 scopus 로고
    • α-deprotecting reagent for the fluorenylmethoxycarbonyl group in continuous flow solid-phase peptide synthesis
    • α-deprotecting reagent for the fluorenylmethoxycarbonyl group in continuous flow solid-phase peptide synthesis. Peptide Res. 1991; 4: 194-199.
    • (1991) Peptide Res. , vol.4 , pp. 194-199
    • Wade, J.D.1    Bedford, J.2    Sheppard, R.C.3    Tregear, G.W.4
  • 175
    • 49549139072 scopus 로고
    • Reactifs de couplage peptidique IV (1) - L'hexafluorophosphate de benzotriazole N-oxytrisdimethylamino phosphonium (B.O.P.)
    • Castro B, Dormoy JR, Evin G, Selve C. Reactifs de couplage peptidique IV (1) - L'hexafluorophosphate de benzotriazole N-oxytrisdimethylamino phosphonium (B.O.P.). Tetrahedron Lett. 1975; 1219-1222.
    • (1975) Tetrahedron Lett. , pp. 1219-1222
    • Castro, B.1    Dormoy, J.R.2    Evin, G.3    Selve, C.4
  • 176
    • 0025678431 scopus 로고
    • Use of BOP reagent for the suppression of diketopiperazine formation in Boc/Bzl solid-phase peptide synthesis
    • Gairi M, Lloyd-Williams P, Albericio F, Giralt E. Use of BOP reagent for the suppression of diketopiperazine formation in Boc/Bzl solid-phase peptide synthesis. Tetrahedron Lett. 1990; 31: 7363-7366.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7363-7366
    • Gairi, M.1    Lloyd-Williams, P.2    Albericio, F.3    Giralt, E.4
  • 177
    • 0013085312 scopus 로고
    • Recent results in convergent solid-phase peptide synthesis
    • ESCOM Science Publishers, B. V.: Leiden
    • Lloyd-Williams P, Gairi M, Cardenas F, Albericio F, Giralt E. Recent results in convergent solid-phase peptide synthesis. In Peptides 1990. ESCOM Science Publishers, B. V.: Leiden, 1991; 146-147.
    • (1991) Peptides 1990 , pp. 146-147
    • Lloyd-Williams, P.1    Gairi, M.2    Cardenas, F.3    Albericio, F.4    Giralt, E.5
  • 178
    • 0016607330 scopus 로고
    • Suppression of diketopiperazine formation in solid phase peptide synthesis
    • Suzuki K, Nitta K, Endo N. Suppression of diketopiperazine formation in solid phase peptide synthesis. Chem. Pharm. Bull. 1975; 23: 222-224.
    • (1975) Chem. Pharm. Bull. , vol.23 , pp. 222-224
    • Suzuki, K.1    Nitta, K.2    Endo, N.3
  • 179
    • 0030012632 scopus 로고    scopus 로고
    • tBu solid-phase peptide synthesis using alkoxybenzyl ester anchoring linkages
    • tBu solid-phase peptide synthesis using alkoxybenzyl ester anchoring linkages. Tetrahedron Lett. 1996; 37: 4195-4198.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4195-4198
    • Alsina, J.1    Giralt, E.2    Albericio, F.3
  • 180
    • 33845312505 scopus 로고
    • Advantageous applications of azabenzotrazole (triazolopyridine)-based coupling reagents to solid-phase peptide synthesis
    • Carpino LA, El-Faham A, Minor CA, Albericio F. Advantageous applications of azabenzotrazole (triazolopyridine)-based coupling reagents to solid-phase peptide synthesis. J. Chem. Soc. Chem. Commun. 1994; 201-203.
    • (1994) J. Chem. Soc. Chem. Commun. , pp. 201-203
    • Carpino, L.A.1    El-Faham, A.2    Minor, C.A.3    Albericio, F.4
  • 181
    • 0022091975 scopus 로고
    • α-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters and solid-phase peptide synthesis
    • α-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters and solid-phase peptide synthesis. Int. J. Peptide Protein Res. 1985; 26: 92-97.
    • (1985) Int. J. Peptide Protein Res. , vol.26 , pp. 92-97
    • Albericio, F.1    Barany, G.2
  • 182
    • 0026783997 scopus 로고
    • Use of N-Fmoc amino acid chlorides and activated 2-(fluorenylmethoxy)-5(4H)-oxazolones in solid-phase peptide synthesis. Efficient synthesis of highly N-alkylated cyclic hexapeptide oxytocin antagonists related to L-365,209
    • Perlow DS, Erb JM, Gould NP, Tung RD, Freidinger RM, Williams PD, Veber DF. Use of N-Fmoc amino acid chlorides and activated 2-(fluorenylmethoxy)-5(4H)-oxazolones in solid-phase peptide synthesis. Efficient synthesis of highly N-alkylated cyclic hexapeptide oxytocin antagonists related to L-365,209. J. Org. Chem. 1992; 57: 4394-4400.
    • (1992) J. Org. Chem. , vol.57 , pp. 4394-4400
    • Perlow, D.S.1    Erb, J.M.2    Gould, N.P.3    Tung, R.D.4    Freidinger, R.M.5    Williams, P.D.6    Veber, D.F.7
  • 183
    • 0002756243 scopus 로고
    • Prevention of diketopiperazine formation in peptide synthesis by simultaneous deprotection-coupling procedure: Entrapment of reactive nucleophilic species by in situ acylation
    • Shute RE, Rich DH. Prevention of diketopiperazine formation in peptide synthesis by simultaneous deprotection-coupling procedure: entrapment of reactive nucleophilic species by in situ acylation. J. Chem. Soc. Chem. Commun. 1987; 1155-1156.
    • (1987) J. Chem. Soc. Chem. Commun. , pp. 1155-1156
    • Shute, R.E.1    Rich, D.H.2
  • 184
    • 0019620780 scopus 로고
    • Synthesis of 2-(trimethylsilyl)ethyloxy-carbonylamino acids and their use in peptide chemistry
    • Wuensch E, Moroder L, Keller O. Synthesis of 2-(trimethylsilyl)ethyloxy-carbonylamino acids and their use in peptide chemistry. Hoppe-Seyler's Z. Physiol. Chem. 1981; 362: 1289-1292.
    • (1981) Hoppe-Seyler's Z. Physiol. Chem. , vol.362 , pp. 1289-1292
    • Wuensch, E.1    Moroder, L.2    Keller, O.3
  • 185
    • 0028833961 scopus 로고
    • Reductive alkylation on a solid phase: Synthesis of a
    • Gordon DW, Steele J. Reductive alkylation on a solid phase: synthesis of a piperazinedione combinatorial library. Bioorg. Med. Chem. Lett. 1995; 5: 47-50.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 47-50
    • Gordon, D.W.1    Steele, J.2
  • 186
    • 0030252432 scopus 로고    scopus 로고
    • Rationally designed non-peptides: Variously substituted piperazine libraries for the discovery of bradykinin antagonists and other G-protein-coupled receptor ligands
    • Goodfellow VS, Laudeman CP, Gerrity JI, Burkard M, Strobel E, Zuzack JS, McLeod DA. Rationally designed non-peptides: variously substituted piperazine libraries for the discovery of bradykinin antagonists and other G-protein-coupled receptor ligands. Mol. Div. 1996; 2: 97-102.
    • (1996) Mol. Div. , vol.2 , pp. 97-102
    • Goodfellow, V.S.1    Laudeman, C.P.2    Gerrity, J.I.3    Burkard, M.4    Strobel, E.5    Zuzack, J.S.6    McLeod, D.A.7
  • 187
    • 0030072545 scopus 로고    scopus 로고
    • Solid phase organic synthesis (SPOS): A novel route to diketopiperazines and diketomorpholines
    • Scott BO, Siegmund AC, Marlowe CK, Pei Y, Spear KL. Solid phase organic synthesis (SPOS): a novel route to diketopiperazines and diketomorpholines. Mol. Div. 1996; 1: 125-134.
    • (1996) Mol. Div. , vol.1 , pp. 125-134
    • Scott, B.O.1    Siegmund, A.C.2    Marlowe, C.K.3    Pei, Y.4    Spear, K.L.5
  • 188
    • 0034057752 scopus 로고    scopus 로고
    • Solution-phase synthesis of mixed amide libraries by simultaneous addition of functionalities (SPSAF) to a diketopiperazinetetracarboxylic acid scaffold monitored by GC analysis of isobutyl alcohol
    • Falorni M, Giacomelli G, Porcheddu A, Taddei M. Solution-phase synthesis of mixed amide libraries by simultaneous addition of functionalities (SPSAF) to a diketopiperazinetetracarboxylic acid scaffold monitored by GC analysis of isobutyl alcohol. Eur. J. Org. Chem. 2000; 1669-1675.
    • (2000) Eur. J. Org. Chem. , pp. 1669-1675
    • Falorni, M.1    Giacomelli, G.2    Porcheddu, A.3    Taddei, M.4
  • 189
    • 0031000559 scopus 로고    scopus 로고
    • A simple procedure for the solid phase synthesis of diketopiperazine and diketomorpholine derivatives
    • Szardenings AK, Burkoth TS, Lu HH, Tien DW, Campbell DA. A simple procedure for the solid phase synthesis of diketopiperazine and diketomorpholine derivatives. Tetrahedron 1997; 53: 6573-6593.
    • (1997) Tetrahedron , vol.53 , pp. 6573-6593
    • Szardenings, A.K.1    Burkoth, T.S.2    Lu, H.H.3    Tien, D.W.4    Campbell, D.A.5
  • 192
    • 0035228612 scopus 로고    scopus 로고
    • N-Terminal peptide aldehydes as electrophiles in combinatorial solid phase synthesis of novel peptide isosteres
    • Groth T, Meldal M. N-Terminal peptide aldehydes as electrophiles in combinatorial solid phase synthesis of novel peptide isosteres. J. Comb. Chem. 2001; 3: 45-63.
    • (2001) J. Comb. Chem. , vol.3 , pp. 45-63
    • Groth, T.1    Meldal, M.2
  • 193
    • 0033041516 scopus 로고    scopus 로고
    • In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis
    • Falb E, Yechezkel T, Salitra Y, Gilon C. In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis. J. Peptide Res. 1999; 53: 507-517.
    • (1999) J. Peptide Res. , vol.53 , pp. 507-517
    • Falb, E.1    Yechezkel, T.2    Salitra, Y.3    Gilon, C.4
  • 194
    • 0032503569 scopus 로고    scopus 로고
    • Backbone amide linker strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides
    • Jensen KJ, Alsina J, Songster MF, Vagner J, Albericio F, Barany G. Backbone amide linker strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides. J. Am. Chem. Soc. 1998; 120: 5441-5452.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5441-5452
    • Jensen, K.J.1    Alsina, J.2    Songster, M.F.3    Vagner, J.4    Albericio, F.5    Barany, G.6
  • 195
    • 0033593405 scopus 로고    scopus 로고
    • Cyclization of histidine containing peptides in the solid-phase by anchoring the imidazole ring to trityl resins
    • Sabatino G, Chelli M, Mazzucco S, Ginanneschi M, Papini AM. Cyclization of histidine containing peptides in the solid-phase by anchoring the imidazole ring to trityl resins. Tetrahedron Lett. 1999; 40: 809-812.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 809-812
    • Sabatino, G.1    Chelli, M.2    Mazzucco, S.3    Ginanneschi, M.4    Papini, A.M.5
  • 196
    • 0032559999 scopus 로고    scopus 로고
    • Solid-phase synthesis of diketopiperazines, useful scaffolds for combinatorial chemistry
    • del Fresno M, Alsina J, Royo M. Barany G, Albericio F. Solid-phase synthesis of diketopiperazines, useful scaffolds for combinatorial chemistry. Tetrahedron Lett. 1998; 39: 2639-2642.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2639-2642
    • del Fresno, M.1    Alsina, J.2    Royo, M.3    Barany, G.4    Albericio, F.5
  • 198
    • 0032497430 scopus 로고    scopus 로고
    • Solid-phase synthesis of a library of piperazinediones and diazepinediones via Kaiser oxime resin
    • Smith RA, Bobko MA, Lee W. Solid-phase synthesis of a library of piperazinediones and diazepinediones via Kaiser oxime resin. Bioorg. Med. Chem. Lett. 1998; 8: 2369-2374.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2369-2374
    • Smith, R.A.1    Bobko, M.A.2    Lee, W.3
  • 199
    • 0011551580 scopus 로고    scopus 로고
    • The N-acyliminium Pictet-Spengler condensation as a multicomponent combinatorial reaction on solid phase and its application to the synthesis of demethoxyfumitremorgin C analogues
    • Wang H, Ganesan A. The N-acyliminium Pictet-Spengler condensation as a multicomponent combinatorial reaction on solid phase and its application to the synthesis of demethoxyfumitremorgin C analogues. Org. Lett. 1999; 1: 1647-1649.
    • (1999) Org. Lett. , vol.1 , pp. 1647-1649
    • Wang, H.1    Ganesan, A.2
  • 200
    • 0034615968 scopus 로고    scopus 로고
    • Solid-phase synthesis and structural characterization of highly substituted hydroxyproline-based 2,5-diketopiperazines
    • Bianco A, Sonksen CP, Roepstorff P, Briand J-P. Solid-phase synthesis and structural characterization of highly substituted hydroxyproline-based 2,5-diketopiperazines. J. Org. Chem. 2000; 65: 2179-2187.
    • (2000) J. Org. Chem. , vol.65 , pp. 2179-2187
    • Bianco, A.1    Sonksen, C.P.2    Roepstorff, P.3    Briand, J-.P.4
  • 201
    • 0027940148 scopus 로고
    • Straightforward and general method for coupling alcohols to solid supports
    • Thompson LA, Ellman JA. Straightforward and general method for coupling alcohols to solid supports. Tetrahedron Lett. 1994; 35: 9333-9336.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9333-9336
    • Thompson, L.A.1    Ellman, J.A.2
  • 202
    • 0000128910 scopus 로고    scopus 로고
    • Multistep synthesis of 2,5-diketopiperazines on different solid supports monitored by high resolution magic angle spinning NMR spectroscopy
    • Bianco A, Furrer J, Limal D, Guichard G, Elbayed K, Raya J, Piotto M, Briand J-P. Multistep synthesis of 2,5-diketopiperazines on different solid supports monitored by high resolution magic angle spinning NMR spectroscopy. J. Comb. Chem. 2000; 2: 681-690.
    • (2000) J. Comb. Chem. , vol.2 , pp. 681-690
    • Bianco, A.1    Furrer, J.2    Limal, D.3    Guichard, G.4    Elbayed, K.5    Raya, J.6    Piotto, M.7    Briand, J.-P.8
  • 203
    • 0030593595 scopus 로고    scopus 로고
    • POEPOP and POEPS: Inert polyethylene glycol crosslinked polymeric supports for solid synthesis
    • Renil M, Meldal M. POEPOP and POEPS: inert polyethylene glycol crosslinked polymeric supports for solid synthesis. Tetrahedron Lett. 1996; 37: 6185-6188.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6185-6188
    • Renil, M.1    Meldal, M.2
  • 204
    • 0032485439 scopus 로고    scopus 로고
    • The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: Novel application of Armstrong's convertible isonitrile
    • Hulme C, Morrissette MM, Volz FA, Burns CJ. The solution phase synthesis of diketopiperazine libraries via the Ugi reaction: novel application of Armstrong's convertible isonitrile. Tetrahedron Lett. 1998; 39: 1113-1116.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1113-1116
    • Hulme, C.1    Morrissette, M.M.2    Volz, F.A.3    Burns, C.J.4
  • 205
    • 0030603133 scopus 로고    scopus 로고
    • Ugi reactions with trifunctional α-amino acids, aldehydes, isocyanides and alcohols
    • Ugi I, Demharter A, Hoerl W, Schmid T. Ugi reactions with trifunctional α-amino acids, aldehydes, isocyanides and alcohols. Tetrahedron 1996; 52: 11657-11664.
    • (1996) Tetrahedron , vol.52 , pp. 11657-11664
    • Ugi, I.1    Demharter, A.2    Hoerl, W.3    Schmid, T.4
  • 207
    • 0033575465 scopus 로고    scopus 로고
    • Novel applications of ethyl glyoxalate with the Ugi MCR
    • Hulme C, Cherrier MP. Novel applications of ethyl glyoxalate with the Ugi MCR. Tetrahedron Lett. 1999; 40: 5295-5299.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5295-5299
    • Hulme, C.1    Cherrier, M.P.2
  • 208
    • 0001534308 scopus 로고    scopus 로고
    • Novel solution- and solid-phase strategies for the parallel and combinatorial synthesis of low-molecular-weight compound libraries
    • Chucholowski A, Masquelin T, Obrecht D, Stadlwieser J, Villalgordo JM. Novel solution- and solid-phase strategies for the parallel and combinatorial synthesis of low-molecular-weight compound libraries. Chimia 1996; 50: 525-530.
    • (1996) Chimia , vol.50 , pp. 525-530
    • Chucholowski, A.1    Masquelin, T.2    Obrecht, D.3    Stadlwieser, J.4    Villalgordo, J.M.5
  • 211
    • 0037018444 scopus 로고    scopus 로고
    • A new resin-bound universal isonitrile for the Ugi 4CC reaction: Preparation and applications to the synthesis of 2,5-diketopiperazines and 1.4-benzodiazepine-2,5-diones
    • Kennedy AL, Fryer AM, Josey JA. A new resin-bound universal isonitrile for the Ugi 4CC reaction: preparation and applications to the synthesis of 2,5-diketopiperazines and 1.4-benzodiazepine-2,5-diones. Org. Lett. 2002; 4: 1167-1170.
    • (2002) Org. Lett. , vol.4 , pp. 1167-1170
    • Kennedy, A.L.1    Fryer, A.M.2    Josey, J.A.3
  • 212
    • 0013093494 scopus 로고    scopus 로고
    • New reactions of alkenyl-boronic acids
    • Petasis NA, Zavialov IA. New reactions of alkenyl-boronic acids. Adv. Boron Chem. 1997; 201: 179-182.
    • (1997) Adv. Boron. Chem. , vol.201 , pp. 179-182
    • Petasis, N.A.1    Zavialov, I.A.2
  • 213
    • 0034686345 scopus 로고    scopus 로고
    • Solid supported high-throughput organic synthesis of peptide β-turn mimetics via tandem Petasis reaction/diketopiperazine formation
    • Golebiowski A, Klopfenstein SR, Chen JJ, Shao X. Solid supported high-throughput organic synthesis of peptide β-turn mimetics via tandem Petasis reaction/diketopiperazine formation. Tetrahedron Lett. 2000; 41: 4841-4844.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4841-4844
    • Golebiowski, A.1    Klopfenstein, S.R.2    Chen, J.J.3    Shao, X.4
  • 214
    • 0027231813 scopus 로고
    • Alewood PF, Andrews PR. β- Turn topography
    • Ball JB, Hughes RA, Alewood PF, Andrews PR. β- Turn topography. Tetrahedron 1993; 49: 3467-3478.
    • (1993) Tetrahedron , vol.49 , pp. 3467-3478
    • Ball, J.B.1    Hughes, R.A.2
  • 215
    • 0010036491 scopus 로고    scopus 로고
    • 3-Ylidenepiperazine-2,5-diones as versatile organic substrates
    • Liebscher J, Jin S. 3-Ylidenepiperazine-2,5-diones as versatile organic substrates. Chem. Soc. Rev. 1999; 28: 251-259.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 251-259
    • Liebscher, J.1    Jin, S.2
  • 216
    • 0034677118 scopus 로고    scopus 로고
    • Solution-phase combinatorial synthesis and evaluation of piperazine-2,5-dione derivatives
    • Loughlin WA, Marshall RL, Carreiro A, Elson KE. Solution-phase combinatorial synthesis and evaluation of piperazine-2,5-dione derivatives. Bioorg. Med. Chem. Lett. 2000; 10: 91-94.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 91-94
    • Loughlin, W.A.1    Marshall, R.L.2    Carreiro, A.3    Elson, K.E.4
  • 217
    • 0036512408 scopus 로고    scopus 로고
    • Solid-phase synthesis of unsaturated 3-substituted piperazine-2,5-diones
    • Li W-R, Yang JH. Solid-phase synthesis of unsaturated 3-substituted piperazine-2,5-diones. J. Comb. Chem. 2002; 4: 106-108.
    • (2002) J. Comb. Chem. , vol.4 , pp. 106-108
    • Li, W.-R.1    Yang, J.H.2


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