메뉴 건너뛰기




Volumn 43, Issue 36, 2002, Pages 6473-6477

Synthesis of cyclic β-turn mimics from L-Pro-Phe/Phe-L-Pro derived di- and tripeptides via ring closing metathesis: The role of chirality of the Phe residue during cyclization

Author keywords

[No Author keywords available]

Indexed keywords

4,5 DEHYDRO 6 AMINOCAPROIC ACID; AMIDE; AMINO ACID; GLYCINE DERIVATIVE; HEXANOIC ACID DERIVATIVE; PHENYLALANINE DERIVATIVE; PROLINE DERIVATIVE; TRIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037009734     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01238-8     Document Type: Article
Times cited : (17)

References (31)
  • 4
    • 0011099170 scopus 로고    scopus 로고
    • Goodman, M.; Ro, S. Berger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; 1995; Vol. 1: Principles and Practice.
  • 10
    • 0000327897 scopus 로고
    • E.J. Ariens. New York: Academic
    • Farmer P.S. Ariens E.J., Drug Design. 10:1980;119-143 Academic, New York.
    • (1980) Drug Design , vol.10 , pp. 119-143
    • Farmer, P.S.1
  • 20
    • 0011132595 scopus 로고    scopus 로고
    • General procedure of amide coupling: To a stirred solution of pent-4-enoyl-XAA acid in THF at 0°C was added triethylamine (1 equiv.), followed by isobutyl chloroformate (1 equiv.) and the mixture vigorously stirred for 5 min and then finally to this was added XA′A′-allyl amide followed by triethylamine (1 equiv.). The reaction mixture was stirred for 5 h at rt and after that the solvent was removed, the residue taken up in ethyl acetate, washed with sodium bicarbonate and saturated citric acid solution and finally with brine. Drying over sodium sulfate, then concentration in vacuo yielded the crude peptide, which was subjected to column chromatography (silica gel, EtOAc:hexane) to afford the desired peptide in good yields.
    • General procedure of amide coupling: To a stirred solution of pent-4-enoyl-XAA acid in THF at 0°C was added triethylamine (1 equiv.), followed by isobutyl chloroformate (1 equiv.) and the mixture vigorously stirred for 5 min and then finally to this was added XA′A′-allyl amide followed by triethylamine (1 equiv.). The reaction mixture was stirred for 5 h at rt and after that the solvent was removed, the residue taken up in ethyl acetate, washed with sodium bicarbonate and saturated citric acid solution and finally with brine. Drying over sodium sulfate, then concentration in vacuo yielded the crude peptide, which was subjected to column chromatography (silica gel, EtOAc:hexane) to afford the desired peptide in good yields.
  • 23
    • 0344006321 scopus 로고    scopus 로고
    • and references cited therein
    • Furstner A. Angew. Chem., Int. Ed. 39:2000;3012-3043. and references cited therein.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3012-3043
    • Furstner, A.1
  • 28
    • 0033549679 scopus 로고    scopus 로고
    • For CD spectra of β-turns see: (a) Furness, K.; Aube, J. Org. Lett. 1999, 1, 495; (b) Venkatachalam, C. M. Biopolymers 1968, 6, 1425; (c) MacDonald, M.; Aube, J. Current Org. Chem. 2001, 5, 417.
    • (1999) Org. Lett. , vol.1 , pp. 495
    • Furness, K.1    Aube, J.2
  • 29
    • 0014347799 scopus 로고
    • For CD spectra of β-turns see: (a) Furness, K.; Aube, J. Org. Lett. 1999, 1, 495; (b) Venkatachalam, C. M. Biopolymers 1968, 6, 1425; (c) MacDonald, M.; Aube, J. Current Org. Chem. 2001, 5, 417.
    • (1968) Biopolymers , vol.6 , pp. 1425
    • Venkatachalam, C.M.1
  • 30
    • 17744399693 scopus 로고    scopus 로고
    • For CD spectra of β-turns see: (a) Furness, K.; Aube, J. Org. Lett. 1999, 1, 495; (b) Venkatachalam, C. M. Biopolymers 1968, 6, 1425; (c) MacDonald, M.; Aube, J. Current Org. Chem. 2001, 5, 417.
    • (2001) Current Org. Chem. , vol.5 , pp. 417
    • MacDonald, M.1    Aube, J.2
  • 31
    • 0011070358 scopus 로고    scopus 로고
    • note
    • -1): 3322, 1639, 1542, 1449.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.