Nucleation of β-hairpin structures with cis amide bonds in E-vinylogous proline-containing peptides

Journal of Organic Chemistry

Volumn 68, Issue 16, 2003, Pages 6459-6462

  Chakraborty, Tushar K ^a   Ghosh, Animesh ^a   Kumar, S Kiran ^a   Kunwar, Ajit C ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE BONDS;

CONFORMATIONS; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEATION; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

AMIDE; BUTOXYCARBONYLALANYLVALYLVINYLPROLYLGLYCYLLEUCINE O METHYL ESTER; BUTOXYCARBONYLALANYLVALYLVINYLPROLYLPHENYLALANYLLEUCINE O METHYL ESTER; BUTOXYCARBONYLLEUCYLISOLEUCYLVALYLVINYLPROLYLGLYCINE O METHYL ESTER; BUTOXYCARBONYLLEUCYLISOLEUCYLVALYLVINYLPROLYLPHENYLALANYLLEUCINE O METHYL ESTER; PEPTIDE; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; BETA SHEET; CHEMICAL BOND; HYDROGEN BOND; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN STRUCTURE; STRUCTURE ANALYSIS;

HYDROGEN BONDING; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NUCLEIC ACID CONFORMATION; PEPTIDES; PROLINE;

EID: 0041573426     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034361j     Document Type: Article

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40. For some leading references on intramolecular hydrogen bonding in small peptides see: (a) Fisk, J. D.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 5443-5447. (b) Chitnumsub, P.; Fiori, W. R.; Lashuel, H. A.; Diaz, H.; Kelly, J. W. Bioorg. Med. Chem. 1999, 7, 39-59. (c) Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482-6483. (d) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89-99. (e) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988-4005. (f) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173.
41. For some leading references on intramolecular hydrogen bonding in small peptides see: (a) Fisk, J. D.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 5443-5447. (b) Chitnumsub, P.; Fiori, W. R.; Lashuel, H. A.; Diaz, H.; Kelly, J. W. Bioorg. Med. Chem. 1999, 7, 39-59. (c) Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482-6483. (d) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89-99. (e) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988-4005. (f) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173.
42. For some leading references on intramolecular hydrogen bonding in small peptides see: (a) Fisk, J. D.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 5443-5447. (b) Chitnumsub, P.; Fiori, W. R.; Lashuel, H. A.; Diaz, H.; Kelly, J. W. Bioorg. Med. Chem. 1999, 7, 39-59. (c) Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482-6483. (d) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89-99. (e) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988-4005. (f) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173.
43. For some leading references on intramolecular hydrogen bonding in small peptides see: (a) Fisk, J. D.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 5443-5447. (b) Chitnumsub, P.; Fiori, W. R.; Lashuel, H. A.; Diaz, H.; Kelly, J. W. Bioorg. Med. Chem. 1999, 7, 39-59. (c) Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482-6483. (d) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89-99. (e) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988-4005. (f) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173.
44. For some leading references on intramolecular hydrogen bonding in small peptides see: (a) Fisk, J. D.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 5443-5447. (b) Chitnumsub, P.; Fiori, W. R.; Lashuel, H. A.; Diaz, H.; Kelly, J. W. Bioorg. Med. Chem. 1999, 7, 39-59. (c) Gung, B. W.; Zhu, Z. J. Org. Chem. 1996, 61, 6482-6483. (d) Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89-99. (e) Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988-4005. (f) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173.
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