메뉴 건너뛰기




Volumn 3, Issue 2, 1997, Pages 110-122

Conformational characterization of the 1-aminocyclobutane-1-carboxylic acid residue in model peptides

Author keywords

310 helix; Cyclic amino acid; Peptide conformation, x ray diffraction; bend

Indexed keywords

1 AMINOCYCLOBUTANECARBOXYLIC ACID; 1-AMINOCYCLOBUTANECARBOXYLIC ACID; AMINO ACID; PEPTIDE;

EID: 0031085711     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-1387(199703)3:2<110::aid-psc88>3.0.co;2-6     Document Type: Article
Times cited : (51)

References (55)
  • 1
    • 0000598509 scopus 로고
    • N. Kharasch, Ed., Gordon and Breach, New York
    • G. R. Marshall in: Intra-Science Chemistry Report, N. Kharasch, Ed., p. 305-316, Gordon and Breach, New York 1971.
    • (1971) Intra-Science Chemistry Report , pp. 305-316
    • Marshall, G.R.1
  • 2
    • 0025345233 scopus 로고
    • Structural characteristics of α-helical peptide molecules containing Aib residues
    • I. L. Karle and P. Balaram (1990). Structural characteristics of α-helical peptide molecules containing Aib residues. Biochemistry 29, 6747-6756.
    • (1990) Biochemistry , vol.29 , pp. 6747-6756
    • Karle, I.L.1    Balaram, P.2
  • 3
    • 0026419837 scopus 로고
    • Structures of polypeptides from α-amino acids disubstituted at the α-carbon
    • C. Toniolo and E. Benedetti (1991). Structures of polypeptides from α-amino acids disubstituted at the α-carbon. Macromolecules 24, 4004-4009.
    • (1991) Macromolecules , vol.24 , pp. 4004-4009
    • Toniolo, C.1    Benedetti, E.2
  • 4
    • 0001210551 scopus 로고
    • Non-standard amino acids in peptide design and protein engineering
    • P. Balaram (1992). Non-standard amino acids in peptide design and protein engineering. Current Opin. Struct. Biol. 2, 845-851.
    • (1992) Current Opin. Struct. Biol. , vol.2 , pp. 845-851
    • Balaram, P.1
  • 5
    • 0001792085 scopus 로고
    • α,α-Symmetrically disubstituted glycines: Useful building blocks in the design of conformationally restricted peptides
    • α,α-Symmetrically disubstituted glycines: useful building blocks in the design of conformationally restricted peptides. Janssen Chim. Acta 11, 10-16.
    • (1993) Janssen Chim. Acta , vol.11 , pp. 10-16
    • Toniolo, C.1
  • 6
    • 0017435119 scopus 로고
    • Conformational analysis of the 20 naturally occurring amino acid residues using ECEPP
    • S. S. Zimmerman, M. S. Pottle, G. Nemethy and H. A. Scheraga (1977). Conformational analysis of the 20 naturally occurring amino acid residues using ECEPP. Macromolecules 10, 1-9.
    • (1977) Macromolecules , vol.10 , pp. 1-9
    • Zimmerman, S.S.1    Pottle, M.S.2    Nemethy, G.3    Scheraga, H.A.4
  • 7
    • 0014347799 scopus 로고
    • Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three-linked peptide units
    • C. M. Venkatachalam (1968). Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three-linked peptide units. Biopolymers 6, 1425-1436.
    • (1968) Biopolymers , vol.6 , pp. 1425-1436
    • Venkatachalam, C.M.1
  • 8
    • 0019267144 scopus 로고
    • Intramolecularly hydrogen-bonded peptide conformations
    • C. Toniolo (1980). Intramolecularly hydrogen-bonded peptide conformations. CRC Crit. Rev. Biochem. 9, 1-44.
    • (1980) CRC Crit. Rev. Biochem. , vol.9 , pp. 1-44
    • Toniolo, C.1
  • 11
    • 0343437835 scopus 로고
    • 1-Aminocyclobutane carboxylic acid hydrochloride monohydrate
    • K. K. Chacko and R. Zand (1975). 1-Aminocyclobutane carboxylic acid hydrochloride monohydrate. Cryst. Struct. Commun. 4, 17-19.
    • (1975) Cryst. Struct. Commun. , vol.4 , pp. 17-19
    • Chacko, K.K.1    Zand, R.2
  • 12
    • 0023851975 scopus 로고
    • Konformationsanalysen von Modell-Tripeptides: Der Einfluss von α,α-disubstituierten α-Aminosäuren auf die Sekundarstruktur. Teil I. NMR- und CD-Untersuchungen
    • P. Wipf and H. Heimgartner (1988). Konformationsanalysen von Modell-Tripeptides: Der Einfluss von α,α-disubstituierten α-Aminosäuren auf die Sekundarstruktur. Teil I. NMR- und CD-Untersuchungen. Helv. Chim. Acta 71, 258-267.
    • (1988) Helv. Chim. Acta , vol.71 , pp. 258-267
    • Wipf, P.1    Heimgartner, H.2
  • 13
    • 0029303265 scopus 로고
    • Conformational studies on model peptides with 1-aminocyclobutane-1-carboxylic acid residues
    • V. N. Balaji, K. Ramnarayan, M. F. Chan and S. N. Rao (1995). Conformational studies on model peptides with 1-aminocyclobutane-1-carboxylic acid residues. Pept. Res. 8, 178-186.
    • (1995) Pept. Res. , vol.8 , pp. 178-186
    • Balaji, V.N.1    Ramnarayan, K.2    Chan, M.F.3    Rao, S.N.4
  • 14
    • 0001312299 scopus 로고
    • The γ-turn, a possible folded conformation of the polypeptide chain. Comparison with the β-turn
    • G. Nemethy and M. P. Printz (1972). The γ-turn, a possible folded conformation of the polypeptide chain. Comparison with the β-turn. Macromolecules 5, 755-758.
    • (1972) Macromolecules , vol.5 , pp. 755-758
    • Nemethy, G.1    Printz, M.P.2
  • 16
    • 3042932833 scopus 로고    scopus 로고
    • B. A. Frenz and Associates, Inc. SDP (Structure Determination Package), College Station, Texas, and Enraf-Nonius, Delft, The Netherlands 1985
    • B. A. Frenz and Associates, Inc. SDP (Structure Determination Package), College Station, Texas, and Enraf-Nonius, Delft, The Netherlands 1985.
  • 17
    • 37049062350 scopus 로고
    • Some derivatives of 1-aminocyclopentanecarboxylic acid and related compounds
    • T. A. Connors and W. C. J. Ross (1960). Some derivatives of 1-aminocyclopentanecarboxylic acid and related compounds. J. Chem. Soc., 2119-2132.
    • (1960) J. Chem. Soc. , pp. 2119-2132
    • Connors, T.A.1    Ross, W.C.J.2
  • 18
    • 3043004127 scopus 로고
    • Synthesis of 1-aminocyclobutanecarboxylic acid
    • R. Sudo and S. Ichihara (1963). Synthesis of 1-aminocyclobutanecarboxylic acid. Bull. Chem. Soc. Jpn 36, 145-147.
    • (1963) Bull. Chem. Soc. Jpn , vol.36 , pp. 145-147
    • Sudo, R.1    Ichihara, S.2
  • 19
    • 0344711407 scopus 로고
    • Preparation of new amino acids and 2,5-oxazolidinediones
    • W. Dvonch, H. Fletcher III and H. E. Album (1964). Preparation of new amino acids and 2,5-oxazolidinediones. J. Org. Chem. 29, 2764-2765.
    • (1964) J. Org. Chem. , vol.29 , pp. 2764-2765
    • Dvonch, W.1    Fletcher III, H.2    Album, H.E.3
  • 20
    • 0002657653 scopus 로고
    • Beziehungen zwisches Struktur and Geschmack bei Aminosäuren mit cyclischen Seitenketten
    • R. Treleano, H. D. Belitz, H. Jugel and H. Wieser (1978). Beziehungen zwisches Struktur and Geschmack bei Aminosäuren mit cyclischen Seitenketten. Z. Lebensm. Unters. Forsch. 167, 320-323.
    • (1978) Z. Lebensm. Unters. Forsch. , vol.167 , pp. 320-323
    • Treleano, R.1    Belitz, H.D.2    Jugel, H.3    Wieser, H.4
  • 21
    • 0021713302 scopus 로고
    • Peptide sweeteners. Structural studies on the C-terminal amino acid of L-aspartyl peptide sweeteners
    • J. W. Tsang, B. Schmied, R. Nyfeler and M. Goodman (1984). Peptide sweeteners. Structural studies on the C-terminal amino acid of L-aspartyl peptide sweeteners. J. Med. Chem. 27, 1663-1668.
    • (1984) J. Med. Chem. , vol.27 , pp. 1663-1668
    • Tsang, J.W.1    Schmied, B.2    Nyfeler, R.3    Goodman, M.4
  • 22
    • 33846881470 scopus 로고
    • Aminoacids of the cyclobutane series
    • F. Avotins (1993). Aminoacids of the cyclobutane series. Russian Chem. Rev. 62, 897-906.
    • (1993) Russian Chem. Rev. , vol.62 , pp. 897-906
    • Avotins, F.1
  • 23
    • 0028939976 scopus 로고
    • N, N-Dialkoxycarbonylamino acids from the sodium hydride-mediated reaction of alkyl chloroformates with mixed anhydride of N-alkoxycarbonylamino acids
    • N. L. Benoiton, D. Akyurekll and F. M. F. Chen (1995). N, N-Dialkoxycarbonylamino acids from the sodium hydride-mediated reaction of alkyl chloroformates with mixed anhydride of N-alkoxycarbonylamino acids. Int. J. Pept. Protein Res. 45, 466-470.
    • (1995) Int. J. Pept. Protein Res. , vol.45 , pp. 466-470
    • Benoiton, N.L.1    Akyurekll, D.2    Chen, F.M.F.3
  • 24
    • 84987470039 scopus 로고
    • Selective Amidspaltung bei Peptiden mit α,α-disubstituierten α-Aminosäuren
    • P. Wipf and H. Heimgartner (1987). Selective Amidspaltung bei Peptiden mit α,α-disubstituierten α-Aminosäuren. Helv. Chim. Acta 70, 354-368.
    • (1987) Helv. Chim. Acta , vol.70 , pp. 354-368
    • Wipf, P.1    Heimgartner, H.2
  • 25
    • 84986401786 scopus 로고
    • Anwendung der Azirin-Oxazolon-Methode in der Peptid-Chemie: Synthese von Modell-Tripeptiden
    • P. Wipf and H. Heimgartner (1988). Anwendung der Azirin-Oxazolon-Methode in der Peptid-Chemie: Synthese von Modell-Tripeptiden. Helv. Chim. Acta 71, 140-154.
    • (1988) Helv. Chim. Acta , vol.71 , pp. 140-154
    • Wipf, P.1    Heimgartner, H.2
  • 26
    • 0027265488 scopus 로고
    • Synthesis of a novel heterospirocyclic 3-(N-methyl-N-phenylamino)2H-azirine and its use as an amino acid equivalent in the preparation of a model tripeptide
    • J. M. Villagordo and H. Heimgartner (1993). Synthesis of a novel heterospirocyclic 3-(N-methyl-N-phenylamino)2H-azirine and its use as an amino acid equivalent in the preparation of a model tripeptide. Tetrahedron 49, 7215-7222.
    • (1993) Tetrahedron , vol.49 , pp. 7215-7222
    • Villagordo, J.M.1    Heimgartner, H.2
  • 27
    • 0001668716 scopus 로고
    • Conformation analysis of linear peptides: 5. Spectroscopic characterization of β-turns in Aib-containing oligopeptides in chloroform
    • G. M. Bonora, C. Mapelli, C. Toniolo, R. R. Wilkening and E. S. Stevens (1984). Conformation analysis of linear peptides: 5. Spectroscopic characterization of β-turns in Aib-containing oligopeptides in chloroform. Int. J. Biol Macromol 6, 179-188.
    • (1984) Int. J. Biol Macromol , vol.6 , pp. 179-188
    • Bonora, G.M.1    Mapelli, C.2    Toniolo, C.3    Wilkening, R.R.4    Stevens, E.S.5
  • 28
    • 0014591979 scopus 로고
    • Conformations of cyclic peptides. IV. Nuclear magnetic resonance studies of cyclopentaglycyl-L-leucyl and cyclodigycyl-L-histidyldiglycyl-L-tyrosyl
    • K. D. Kopple and M. Ohnishi (1969). Conformations of cyclic peptides. IV. Nuclear magnetic resonance studies of cyclopentaglycyl-L-leucyl and cyclodigycyl-L-histidyldiglycyl-L-tyrosyl. Biochemistry 8, 4087-4095.
    • (1969) Biochemistry , vol.8 , pp. 4087-4095
    • Kopple, K.D.1    Ohnishi, M.2
  • 30
    • 0015513701 scopus 로고
    • Proton magnetic resonance line broadening produced by association with a nitroxide radical in studies of amide and peptide conformation
    • K. D. Kopple and T. J. Schamper (1972). Proton magnetic resonance line broadening produced by association with a nitroxide radical in studies of amide and peptide conformation. J. Am. Chem. Soc. 94, 3644-3646.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 3644-3646
    • Kopple, K.D.1    Schamper, T.J.2
  • 33
    • 0014842661 scopus 로고
    • Abbreviations and symbols for the description of the conformation of polypeptide chains
    • IUPAC-IUB Commission of Biochemical Nomenclature (1970). Abbreviations and symbols for the description of the conformation of polypeptide chains. Biochemistry 9, 3471-3479.
    • (1970) Biochemistry , vol.9 , pp. 3471-3479
  • 35
    • 84910512028 scopus 로고
    • Structural characteristics of the carboxylic ester group
    • W. B. Schweizer and J. D. Dunitz (1982). Structural characteristics of the carboxylic ester group. Helv. Chim. Acta 65, 1547-1554.
    • (1982) Helv. Chim. Acta , vol.65 , pp. 1547-1554
    • Schweizer, W.B.1    Dunitz, J.D.2
  • 37
    • 84942963631 scopus 로고
    • Peptlde chain structure parameters, bond angles and conformational angles from the Cambridge structural database
    • T. Ashida, Y. Tsunogae, I. Tanaka and T. Yamane (1987). Peptlde chain structure parameters, bond angles and conformational angles from the Cambridge structural database. Acta Crystallogr. B43, 212-218.
    • (1987) Acta Crystallogr. , vol.B43 , pp. 212-218
    • Ashida, T.1    Tsunogae, Y.2    Tanaka, I.3    Yamane, T.4
  • 38
    • 11344284526 scopus 로고
    • Tables of bonds lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds
    • F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen and R. Taylor (1987). Tables of bonds lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds. J. Chem. Soc., Perkin Trans. 2, S1-S19.
    • (1987) J. Chem. Soc., Perkin Trans. , vol.2
    • Allen, F.H.1    Kennard, O.2    Watson, D.G.3    Brammer, L.4    Orpen, A.G.5    Taylor, R.6
  • 39
    • 0004402822 scopus 로고
    • The crystal structure of 2.2.4.4-tetramethyl-1,3-cyclobutanedithione
    • C. D. Shirrell and D. E. Williams (1973). The crystal structure of 2.2.4.4-tetramethyl-1,3-cyclobutanedithione. Acta Crystallogr. B29, 1648-1653.
    • (1973) Acta Crystallogr. , vol.B29 , pp. 1648-1653
    • Shirrell, C.D.1    Williams, D.E.2
  • 40
    • 0000270788 scopus 로고
    • Sensitivity of polypeptide conformation to geometry. Theoretical conformational analysis of oligomers of α-aminoisobutyric acid
    • Y. Paterson, S. M. Rumsey, E. Benedetti, G. Nemethy and H. A. Scheraga (1981). Sensitivity of polypeptide conformation to geometry. Theoretical conformational analysis of oligomers of α-aminoisobutyric acid. J. Am. Chem. Soc. 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
  • 41
    • 0015173698 scopus 로고
    • Study of hydrogen bonds in amino acids and peptides
    • C. Ramakrishnan and N. Prasad (1971). Study of hydrogen bonds in amino acids and peptides. Int. J. Protein Res. 3, 209-231.
    • (1971) Int. J. Protein Res. , vol.3 , pp. 209-231
    • Ramakrishnan, C.1    Prasad, N.2
  • 42
    • 84977288315 scopus 로고
    • The geometry of the N-H...O = C hydrogen bond. 3. Hydrogen-bond distances and angles
    • R. Taylor, O. Kennard and W. Versichel (1984). The geometry of the N-H...O = C hydrogen bond. 3. Hydrogen-bond distances and angles. Acta CrystaUogr. B40, 280-288.
    • (1984) Acta CrystaUogr. , vol.B40 , pp. 280-288
    • Taylor, R.1    Kennard, O.2    Versichel, W.3
  • 43
    • 0000809197 scopus 로고
    • Hydrogen-bond distances and angles in the structures of amino acids and peptides
    • C. H. Gorbitz (1989). Hydrogen-bond distances and angles in the structures of amino acids and peptides. Acta Crystallogr. B45, 390-395.
    • (1989) Acta Crystallogr. , vol.B45 , pp. 390-395
    • Gorbitz, C.H.1
  • 44
    • 25744472856 scopus 로고
    • Structure of N,N-di-tert-butyloxycarbonyl-glycine N′-methoxy-N′-methylamide
    • J. Lubkowski, L. Lankiewicz and Z. Kosturkiewicz (1992). Structure of N,N-di-tert-butyloxycarbonyl-glycine N′-methoxy-N′-methylamide. Acta Crystallogr. C48, 1616-1619.
    • (1992) Acta Crystallogr. , vol.C48 , pp. 1616-1619
    • Lubkowski, J.1    Lankiewicz, L.2    Kosturkiewicz, Z.3
  • 46
    • 0025336463 scopus 로고
    • Emerging approaches in the molecular design of receptor-selective peptide ligands: Conformational, topographical and dynamic considerations
    • V. J. Hruby, F. Al-Obeidi and W. Kazmierski (1990). Emerging approaches in the molecular design of receptor-selective peptide ligands: conformational, topographical and dynamic considerations. Biochem. J. 268, 249-262.
    • (1990) Biochem. J. , vol.268 , pp. 249-262
    • Hruby, V.J.1    Al-Obeidi, F.2    Kazmierski, W.3
  • 47
    • 0025370346 scopus 로고
    • Conformationally restricted peptides through short-range cyclizations
    • C. Toniolo (1990). Conformationally restricted peptides through short-range cyclizations. Int J. Pept. Protein Res. 35, 287-300.
    • (1990) Int J. Pept. Protein Res. , vol.35 , pp. 287-300
    • Toniolo, C.1
  • 48
    • 0001802703 scopus 로고    scopus 로고
    • Peptide conformation mimetics
    • G. Holzemann (1991). Peptide conformation mimetics. Kontakte (Darmstadt), 3-12 (part 1) and 55-63 (part 2).
    • (1991) Kontakte (Darmstadt) , Issue.1 PART , pp. 3-12
    • Holzemann, G.1
  • 49
    • 0001802703 scopus 로고    scopus 로고
    • G. Holzemann (1991). Peptide conformation mimetics. Kontakte (Darmstadt), 3-12 (part 1) and 55-63 (part 2).
    • Kontakte (Darmstadt) , Issue.2 PART , pp. 55-63
  • 50
    • 33745502124 scopus 로고
    • Peptidomimetics for receptor ligands. Discovery, development, and medical perspectives
    • A. Giannis and T. Kolter (1993). Peptidomimetics for receptor ligands. Discovery, development, and medical perspectives. Angew. Chem. Int. Ed. Engl. 32, 1244-1267.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1244-1267
    • Giannis, A.1    Kolter, T.2
  • 52
    • 0028038601 scopus 로고
    • Peptldomimetics: Taylored enzyme Inhibitors
    • J. Gante (1994). Peptldomimetics: taylored enzyme Inhibitors. Angew. Chem. Int. Ed. Engl 33, 1699-1720.
    • (1994) Angew. Chem. Int. Ed. Engl , vol.33 , pp. 1699-1720
    • Gante, J.1
  • 53
    • 0013534646 scopus 로고
    • Conformationally restricted amino acids and dipeptides, (non)peptidomimetics and secondary structure mimetics
    • R. M. J. Liskamp (1994). Conformationally restricted amino acids and dipeptides, (non)peptidomimetics and secondary structure mimetics. Recl. Trav. Chim. Pays-Bas 113, 1-19.
    • (1994) Recl. Trav. Chim. Pays-Bas , vol.113 , pp. 1-19
    • Liskamp, R.M.J.1
  • 55
    • 0029108642 scopus 로고
    • Probing protein structure and function with an expanded genetic code
    • V. W. Cornish, D. Mendel and P. G. Schultz (1995). Probing protein structure and function with an expanded genetic code. Angew. Chem. Int. Ed. Engl. 34, 621-633.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 621-633
    • Cornish, V.W.1    Mendel, D.2    Schultz, P.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.