메뉴 건너뛰기




Volumn 16, Issue 6, 2010, Pages 284-296

Solution-phase submonomer diversification of aza-dipeptide building blocks and their application in aza-peptide and aza-DKP synthesis

Author keywords

turn conformation; Alkylation; Aza DKP; Aza Gly Xaa; Aza peptide; Benzophenone semicarbazone protecting group; DKP; Triazine

Indexed keywords

AZA DIKETOPIPERAZINE; AZA DIPEPTIDE; AZA PEPTIDE; BENZOPHENONE; DIPEPTIDE; HYDRAZONE DERIVATIVE; PEPTIDE; PIPERAZINE DERIVATIVE; SEMICARBAZONE; UNCLASSIFIED DRUG;

EID: 77953474171     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1235     Document Type: Article
Times cited : (41)

References (51)
  • 1
    • 0019163001 scopus 로고
    • Bioactive conformation of luteinizing hormone-releasing hormone: Evidence from a conformationally constrained analog
    • Freidinger RM, Veber DF, Perlow DS, Brooks JR, Saperstein R. Bioactive conformation of luteinizing hormone-releasing hormone: evidence from a conformationally constrained analog. Science 1980; 210: 656-658.
    • (1980) Science , vol.210 , pp. 656-658
    • Freidinger, R.M.1    Veber, D.F.2    Perlow, D.S.3    Brooks, J.R.4    Saperstein, R.5
  • 2
    • 0019958979 scopus 로고
    • Conformational restrictions of biologically-active peptides via amino-acid side chain groups
    • Hruby VJ. Conformational restrictions of biologically-active peptides via amino-acid side chain groups. Life Sci. 1982; 31: 189-199.
    • (1982) Life Sci. , vol.31 , pp. 189-199
    • Hruby, V.J.1
  • 3
    • 0000515280 scopus 로고
    • Ariens J (ed). Academic: New York
    • Rudinger J. In Drug Design, Vol. 2, Ariens J (ed). Academic: New York, 1971; 319-419.
    • (1971) Drug Design , vol.2 , pp. 319-419
    • Rudinger, J.1
  • 4
    • 0032705432 scopus 로고    scopus 로고
    • Designed molecules that fold to mimic protein secondary structures
    • Stigers KD, Soth MJ, Nowick JS. Designed molecules that fold to mimic protein secondary structures. Curr. Opin. Chem. Biol. 1999; 3: 714-723.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 714-723
    • Stigers, K.D.1    Soth, M.J.2    Nowick, J.S.3
  • 5
    • 85082699866 scopus 로고
    • Azapeptides
    • Gante J. Azapeptides. Synthesis 1989; 405-413.
    • (1989) Synthesis , pp. 405-413
    • Gante, J.1
  • 6
    • 14744297865 scopus 로고    scopus 로고
    • Azapeptides as pharmacological agents
    • Zega A. Azapeptides as pharmacological agents. Curr. Med. Chem. 2005; 12: 589-597.
    • (2005) Curr. Med. Chem. , vol.12 , pp. 589-597
    • Zega, A.1
  • 7
    • 0012782829 scopus 로고
    • N-[2-Isopropyl-3-(L-aspartyl-L-arginyl)-carbazoyl]-L-tyrosyl-L-valyl-L- histidyl-L-prolyl-L-phenylalanine. 1: An Isostere of Bovine Angiotensin II
    • Hess HJ, Moreland WT, Laubach GD. N-[2-Isopropyl-3-(L-aspartyl-L-arginyl) -carbazoyl]-L-tyrosyl-L-valyl-L-histidyl-L-prolyl-L-phenylalanine. 1: an Isostere of Bovine Angiotensin II. J. Am. Chem. Soc. 1963; 85: 4040-4041.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 4040-4041
    • Hess, H.J.1    Moreland, W.T.2    Laubach, G.D.3
  • 8
    • 0018308356 scopus 로고
    • Polypeptides. Part XV. Synthesis and biological-activity of alpha-aza-analogs of Luliberin modified in positions-6 and position-10
    • Dutta AS, Furr BJA, Giles MB. Polypeptides. Part XV. Synthesis and biological-activity of alpha-aza-analogs of Luliberin modified in positions-6 and position-10. J. Chem. Soc. Perkin Trans. 1 1979; 379-388.
    • (1979) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 379-388
    • Dutta, A.S.1    Furr, B.J.A.2    Giles, M.B.3
  • 10
    • 0033918938 scopus 로고    scopus 로고
    • Role of azaamino acid residue in beta-turn formation and stability in designed peptide
    • DOI 10.1034/j.1399-3011.2000.00717.x
    • Lee HJ, Ahn IA, Ro S, Choi KH, Choi YS, Lee KB. Role of azaamino acid residue in beta-turn formation and stability in designed peptide. J. Pept. Res. 2000; 56: 35-46. (Pubitemid 30435436)
    • (2000) Journal of Peptide Research , vol.56 , Issue.1 , pp. 35-46
    • Lee, H.-J.1    Ahn, I.-A.2    Ro, S.3    Choi, K.-H.4    Choi, Y.-S.5    Lee, K.-B.6
  • 11
    • 0035913318 scopus 로고    scopus 로고
    • The beta-turn preferential solution conformation of a tetrapeptide containing an azaamino acid residue
    • DOI 10.1016/S0022-2860(00)00861-9, PII S0022286000008619
    • Lee HJ, Choi KH, Ahn IA, Ro S, Jang HG, Choi YS, Lee KB. The beta-turn preferential solution conformation of a tetrapeptide containing an azaamino acid residue. J. Mol. Struct. 2001; 569: 43-54. (Pubitemid 32660721)
    • (2001) Journal of Molecular Structure , vol.569 , Issue.1-3 , pp. 43-54
    • Lee, H.-J.1    Choi, K.-H.2    Ahn, I.-A.3    Ro, S.4    Jang, H.G.5    Choi, Y.-S.6    Lee, K.-B.7
  • 14
    • 0030773550 scopus 로고    scopus 로고
    • Aza-peptides. III. Experimental structural analysis of aza-alanine and aza-asparagine-containing peptides
    • Andre F, Vicherat A, Boussard G, Aubry A, Marraud M. Aza-peptides. 3. Experimental structural analysis of aza-alanine and aza-asparagine-containing peptides. J. Pept. Res. 1997; 50: 372-381. (Pubitemid 27469143)
    • (1997) Journal of Peptide Research , vol.50 , Issue.5 , pp. 372-381
    • Andre, F.1    Vicherat, A.2    Boussard, G.3    Aubry, A.4    Marraud, M.5
  • 18
    • 0346752006 scopus 로고    scopus 로고
    • Atazanavir: A novel azapeptide inhibitor of HIV-1 protease
    • Wang F, Ross J. Atazanavir: a novel azapeptide inhibitor of HIV-1 protease. Formulary 2003; 38: 691-702. (Pubitemid 37541764)
    • (2003) Formulary , vol.38 , Issue.12 , pp. 691-702
    • Wang, F.1    Ross, J.2
  • 19
    • 0009522508 scopus 로고    scopus 로고
    • Approaches to pseudopeptidic ergopeptines. 3. Consequences of the incorporation of an alpha-azaphenylalanine residue into the ergotamine oxa-cyclolic system
    • Calcagni A, Lucente G, Luisi G, Pinnen F, Rossi D, Gavuzzo E. Approaches to pseudopeptidic ergopeptines. 3. Consequences of the incorporation of an alpha-azaphenylalanine residue into the ergotamine oxa-cyclolic system. J. Chem. Soc. Perkin Trans. 1 1997; 2223-2227.
    • (1997) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 2223-2227
    • Calcagni, A.1    Lucente, G.2    Luisi, G.3    Pinnen, F.4    Rossi, D.5    Gavuzzo, E.6
  • 20
    • 0031263756 scopus 로고    scopus 로고
    • Triphosgene: An efficient carbonylating agent for liquid and solidphase aza-peptide synthesis. Application to the synthesis of two aza-analogues of the AChR MIR decapeptide
    • Andre F, Marraud M, Tsouloufis T, Tzartos SJ, Boussard G. Triphosgene: an efficient carbonylating agent for liquid and solidphase aza-peptide synthesis. Application to the synthesis of two aza-analogues of the AChR MIR decapeptide. J. Pept. Sci. 1997; 3: 429-441.
    • (1997) J. Pept. Sci. , vol.3 , pp. 429-441
    • Andre, F.1    Marraud, M.2    Tsouloufis, T.3    Tzartos, S.J.4    Boussard, G.5
  • 21
    • 2542530630 scopus 로고    scopus 로고
    • Aza-amino acid scan for rapid identification of secondary structure based on the application of N-Boc-aza-dipeptides in peptide synthesis
    • Melendez RE, Lubell WD. Aza-amino acid scan for rapid identification of secondary structure based on the application of N-Boc-aza-dipeptides in peptide synthesis. J. Am. Chem. Soc. 2004; 126: 6759-6764.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 6759-6764
    • Melendez, R.E.1    Lubell, W.D.2
  • 22
    • 28244437082 scopus 로고    scopus 로고
    • Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with Fmoc chemistry and aza-amino acids with heteroatomic side chains
    • Boeglin D, Lubell WD. Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with Fmoc chemistry and aza-amino acids with heteroatomic side chains. J. Comb. Chem. 2005; 7: 864-878.
    • (2005) J. Comb. Chem. , vol.7 , pp. 864-878
    • Boeglin, D.1    Lubell, W.D.2
  • 23
    • 0033214140 scopus 로고    scopus 로고
    • Novel solid-phase synthesis of azapeptides and azapeptoides via Fmoc-strategy and its application in the synthesis of RGD-mimetics
    • Gibson C, Goodman SL, Hahn D, Holzemann G, Kessler H. Novel solid-phase synthesis of azapeptides and azapeptoides via Fmoc-strategy and its application in the synthesis of RGD-mimetics. J. Org. Chem. 1999; 64: 7388-7394.
    • (1999) J. Org. Chem. , vol.64 , pp. 7388-7394
    • Gibson, C.1    Goodman, S.L.2    Hahn, D.3    Holzemann, G.4    Kessler, H.5
  • 24
    • 37049076684 scopus 로고
    • Synthesis of azapeptides by the Fmoc tert-butyl polyamide technique
    • Quibell M, Turnell WG, Johnson T. Synthesis of azapeptides by the Fmoc tert-butyl polyamide technique. J. Chem. Soc. Perkin Trans. 1 1993; 2843-2849.
    • (1993) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 2843-2849
    • Quibell, M.1    Turnell, W.G.2    Johnson, T.3
  • 25
    • 0033546249 scopus 로고    scopus 로고
    • Solid phase urea synthesis: An efficient and direct conversion of Fmoc-protected amines to ureas
    • Chong PY, Petillo PA. Solid phase urea synthesis: an efficient and direct conversion of Fmoc-protected amines to ureas. Tetrahedron Lett. 1999; 40: 4501-4504.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4501-4504
    • Chong, P.Y.1    Petillo, P.A.2
  • 26
    • 0033515726 scopus 로고    scopus 로고
    • Solid-phase synthesis of N,N′-unsymmetrically substituted ureas: Application to the synthesis of carbaza peptides
    • Limal D, Semetey V, Dalbon P, Jolivet M, Briand JP. Solid-phase synthesis of N,N′-unsymmetrically substituted ureas: application to the synthesis of carbaza peptides. Tetrahedron Lett. 1999; 40: 2749-2752.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2749-2752
    • Limal, D.1    Semetey, V.2    Dalbon, P.3    Jolivet, M.4    Briand, J.P.5
  • 27
    • 57249083928 scopus 로고    scopus 로고
    • Synthetic methodology for alkyl substituted hydrazines
    • Ragnarsson U. Synthetic methodology for alkyl substituted hydrazines. Chem. Soc. Rev. 2001; 30: 205-213.
    • (2001) Chem. Soc. Rev. , vol.30 , pp. 205-213
    • Ragnarsson, U.1
  • 28
    • 60849097006 scopus 로고    scopus 로고
    • Benzophenone semicarbazone protection strategy for synthesis of aza-glycine containing azapeptides
    • Bourguet CB, Sabatino D, LubellWD. Benzophenone semicarbazone protection strategy for synthesis of aza-glycine containing azapeptides. Biopolymers 2008; 90: 824-831.
    • (2008) Biopolymers , vol.90 , pp. 824-831
    • Bourguet, C.B.1    Sabatino, D.2    Lubell, W.D.3
  • 30
    • 0034647498 scopus 로고    scopus 로고
    • New synthesis of 1,1-substituted hydrazines by alkylation of N-acyl- Or N-alkyloxycarbonylaminophthalimide using the Mitsunobu protocol
    • Brosse N, Pinto MF, Jamart-Gregoire B. New synthesis of 1,1-substituted hydrazines by alkylation of N-acyl- or N-alkyloxycarbonylaminophthalimide using the Mitsunobu protocol. J. Org. Chem. 2000; 65: 4370-4374.
    • (2000) J. Org. Chem. , vol.65 , pp. 4370-4374
    • Brosse, N.1    Pinto, M.F.2    Jamart-Gregoire, B.3
  • 31
    • 34547985546 scopus 로고    scopus 로고
    • Diketopiperazines: Biological activity and synthesis
    • Martins MB, Carvalho I. Diketopiperazines: biological activity and synthesis. Tetrahedron 2007; 63: 9923-9932.
    • (2007) Tetrahedron , vol.63 , pp. 9923-9932
    • Martins, M.B.1    Carvalho, I.2
  • 32
    • 1842737243 scopus 로고    scopus 로고
    • Liquid and solid phase syntheses of orthogonally protected alpha-hydrazinoacid derivatives
    • DOI 10.1016/j.tetlet.2004.03.063, PII S0040403904005891
    • Bouillon I, Brosse N, Vanderesse R, Jamart-Gregoire B. Liquid and solid phase syntheses of orthogonally protected alpha-hydrazinoacid derivatives. Tetrahedron Lett. 2004; 45: 3569-3572. (Pubitemid 38481728)
    • (2004) Tetrahedron Letters , vol.45 , Issue.18 , pp. 3569-3572
    • Bouillon, I.1    Brosse, N.2    Vanderesse, R.3    Jamart-Gregoire, B.4
  • 33
    • 0035917371 scopus 로고    scopus 로고
    • A new synthetic route to protected alpha-hydrazinoesters in high optical purity using the mitsunobu protocol
    • DOI 10.1021/jo005696t
    • Brosse N, Pinto MF, Bodiguel J, Jamart-Gregoire B. A new synthetic route to protected alpha-hydrazinoesters in high optical purity using the Mitsunobu protocol. J. Org. Chem. 2001; 66: 2869-2873. (Pubitemid 32867712)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.8 , pp. 2869-2873
    • Brosse, N.1    Pinto, M.-F.2    Bodiguel, J.3    Jamart-Gregoire, B.4
  • 34
    • 0034620256 scopus 로고    scopus 로고
    • N-tert-butoxycarbonylaminophthalimide, a versatile reagent for the conversion of alcohols into alkylated tert-butylcarbazates or hydrazines via the Mitsunobu protocol
    • PII S0040403999020389
    • Brosse N, Pinto MF, Jamart-Gregoire B. N-tert- Butoxycarbonylaminophthalimide, a versatile reagent for the conversion of alcohols into alkylated tert-butylcarbazates or hydrazines via the Mitsunobu protocol. Tetrahedron Lett. 2000; 41: 205-207. (Pubitemid 30014602)
    • (2000) Tetrahedron Letters , vol.41 , Issue.2 , pp. 205-207
    • Brosse, N.1    Pinto, M.-F.2    Jamart-Gregoire, B.3
  • 35
    • 0346101624 scopus 로고    scopus 로고
    • Preparation of multiply protected alkylhydrazine derivatives by mitsunobu and PTC approaches
    • Brosse N, Pinto MF, Jamart-Gregoire B. Preparation of multiply protected alkylhydrazine derivatives by mitsunobu and PTC approaches. Eur. J. Org. Chem. 2003; 4757-4764.
    • (2003) Eur. J. Org. Chem. , pp. 4757-4764
    • Brosse, N.1    Pinto, M.F.2    Jamart-Gregoire, B.3
  • 36
    • 0037198779 scopus 로고    scopus 로고
    • Electrochemical imination of sulfoxides using N-aminophthalimide
    • Siu T, Yudin AK. Electrochemical imination of sulfoxides using N-aminophthalimide. Org. Lett. 2002; 4: 1839-1842.
    • (2002) Org. Lett. , vol.4 , pp. 1839-1842
    • Siu, T.1    Yudin, A.K.2
  • 37
    • 0037068629 scopus 로고    scopus 로고
    • Aza-peptides structurally based upon inhibitory sites of cystatins as potent and selective inhibitors of cysteine proteases
    • Wieczerzak E, Drabik P, Lankiewicz L, Oldziej S, Grzonka Z, Abrahamson M, Grubb A, Bromme D. Aza-peptides structurally based upon inhibitory sites of cystatins as potent and selective inhibitors of cysteine proteases. J.Med. Chem. 2002; 45: 4202-4211.
    • (2002) J.Med. Chem. , vol.45 , pp. 4202-4211
    • Wieczerzak, E.1    Drabik, P.2    Lankiewicz, L.3    Oldziej, S.4    Grzonka, Z.5    Abrahamson, M.6    Grubb, A.7    Bromme, D.8
  • 38
    • 4143049107 scopus 로고    scopus 로고
    • The enantioselective synthesis of alpha-amino acids by phase-transfer catalysiswith achiral Schiff base esters
    • O'Donnell MJ. The enantioselective synthesis of alpha-amino acids by phase-transfer catalysiswith achiral Schiff base esters. Acc. Chem. Res. 2004; 37: 506-517.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 506-517
    • O'Donnell, M.J.1
  • 40
    • 77953370411 scopus 로고    scopus 로고
    • Goodman M, Felix A, Moroder L, Toniolo C (eds.) Stuttgart, New York: Thieme (Houben-Weyl)
    • Goodman M, Felix A, Moroder L, Toniolo C (eds.). Methods of Organic Chemistry: Synthesis of Peptides and Peptidomimetics. Stuttgart, New York: Thieme (Houben-Weyl): 2001; 227-228.
    • (2001) Methods of Organic Chemistry: Synthesis of Peptides and Peptidomimetics , pp. 227-228
  • 41
    • 0008978868 scopus 로고
    • T-Butyl esters of amino acids and peptides and their use in peptide synthesis
    • Anderson GW, Callahan FM. t-Butyl esters of amino acids and peptides and their use in peptide synthesis. J. Am. Chem. Soc. 1960; 82: 3359-3363.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 3359-3363
    • Anderson, G.W.1    Callahan, F.M.2
  • 44
    • 0037270158 scopus 로고    scopus 로고
    • A two-step synthesis of hexahydropyrrolo-[1,2-d][1,2,4]triazine-1,4-dione and related compounds
    • DOI 10.1081/SCC-120016366
    • Obreza A, Urleb U. A two-step synthesis of hexahydropyrrolo[1,2-d][1,2,4] triazine-1,4-dione and related compounds. Synth. Commun. 2003; 33: 1011-1018. (Pubitemid 36458748)
    • (2003) Synthetic Communications , vol.33 , Issue.6 , pp. 1011-1018
    • Obreza, A.1    Urleb, U.2
  • 45
    • 37049084966 scopus 로고
    • Approaches to pseudopeptidic ergopeptines-Synthesis and molecular-structure of an alpha-aza-phenylalanine-containing oxa-cyclol
    • Pinnen F, Luisi G, Lucente G, Gavuzzo E, Cerrini S. Approaches to pseudopeptidic ergopeptines-Synthesis and molecular-structure of an alpha-aza-phenylalanine-containing oxa-cyclol. J. Chem. Soc. Perkin Trans. 1 1993; 819-824.
    • (1993) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 819-824
    • Pinnen, F.1    Luisi, G.2    Lucente, G.3    Gavuzzo, E.4    Cerrini, S.5
  • 46
    • 0016417266 scopus 로고
    • Polypeptides. Part XIII. Preparation of alpha-aza-amino-acid (carbazic acid) derivatives and intermediates for the preparation of alpha-aza-peptides
    • Dutta AS, Morley JS. Polypeptides. Part XIII. Preparation of alpha-aza-amino-acid (carbazic acid) derivatives and intermediates for the preparation of alpha-aza-peptides. J. Chem. Soc. Perkin Trans. I 1975; 1712-1720.
    • (1975) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 1712-1720
    • Dutta, A.S.1    Morley, J.S.2
  • 47
    • 0242287992 scopus 로고    scopus 로고
    • Glycosidase inhibitors: Update and perspectives on practical use
    • DOI 10.1093/glycob/cwg090
    • Asano N. Glycosidase inhibitors: update and perspectives on practical use. Glycobiology 2003; 13: 93R-104R. (Pubitemid 37337046)
    • (2003) Glycobiology , vol.13 , Issue.10
    • Asano, N.1
  • 48
    • 10644292508 scopus 로고    scopus 로고
    • Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazapurine and diketopiperazine
    • DOI 10.1081/NCN-200040614
    • Sinha S, Srivastava R, De Clereq E, Singh RK. Synthesis and antiviral properties of arabino and ribonucleosides of 1,3-dideazaadenine, 4-nitro-1,3-dideazapurine and diketopiperazine. Nucleosides Nucleotides Nucleic Acids 2004; 23: 1815-1824. (Pubitemid 39657365)
    • (2004) Nucleosides, Nucleotides and Nucleic Acids , vol.23 , Issue.12 , pp. 1815-1824
    • Sinha, S.1    Srivastava, R.2    De Clercq, E.3    Singh, R.K.4
  • 50
    • 33846708433 scopus 로고    scopus 로고
    • 2,2′:6′,2″-Terpyridines: From chemical obscurity to common supramolecularmotifs
    • Constable EC. 2,2′:6′,2″-Terpyridines: from chemical obscurity to common supramolecularmotifs. Chem. Soc. Rev. 2007; 36: 246-253.
    • (2007) Chem. Soc. Rev. , vol.36 , pp. 246-253
    • Constable, E.C.1
  • 51
    • 58149147150 scopus 로고    scopus 로고
    • Aconvenient synthesisof substituted 2,2′:6′,2″- terpyridines
    • Gehre A, Stanforth SP,Tarbit B.Aconvenient synthesisof substituted 2,2′:6′,2″-terpyridines. Tetrahedron 2009; 65: 1115-1118.
    • (2009) Tetrahedron , vol.65 , pp. 1115-1118
    • Gehre, A.1    Stanforth, S.P.2    Tarbit, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.