Synthesis of the endothiopeptide BOC-Trp-Ile-Ala-Aib-Ile-Valψ[CSNH]Aib-Leu-Aib-Pro-OMe by a variation of the 'azirine/oxazolone method'

被引:43
作者
Lehmann, J [1 ]
Linden, A [1 ]
Heimgartner, H [1 ]
机构
[1] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
关键词
D O I
10.1016/S0040-4020(98)00506-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the decaendothiopeptide BOC-Trp-Ile-Ala-Aib-Ile-Val Psi[CSNH]Aib-Leu-Aib-Pro-OMe is described. The introduction of the thioamide group next to the bulky Aib occurred via a variation of the 'azirine/oxazolone method' without epimerisation. The structure of the decaendothiopeptide was etablished by single-crystal X-ray crystallography, thereby two types of helices could be observed. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:8721 / 8736
页数:16
相关论文
共 44 条
[1]   CONFORMATIONAL STUDIES ON PEPTIDES CONTAINING ENANTIOMERIC ALPHA-METHYL ALPHA-AMINO-ACIDS .1. DIFFERENTIAL CONFORMATIONAL PROPERTIES OF (R)-2-METHYLASPARTIC AND (S)-2-METHYLASPARTIC ACID [J].
ALTMANN, KH ;
ALTMANN, E ;
MUTTER, M .
HELVETICA CHIMICA ACTA, 1992, 75 (04) :1198-1210
[2]  
[Anonymous], 1982, AMINOSAUREN PEPTIDE
[3]   LEAST-SQUARES ABSOLUTE-STRUCTURE REFINEMENT - PRACTICAL EXPERIENCE AND ANCILLARY CALCULATIONS [J].
BERNARDINELLI, G ;
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1985, 41 (SEP) :500-511
[4]   PATTERNS IN HYDROGEN BONDING - FUNCTIONALITY AND GRAPH SET ANALYSIS IN CRYSTALS [J].
BERNSTEIN, J ;
DAVIS, RE ;
SHIMONI, L ;
CHANG, NL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) :1555-1573
[5]   AMINO-ACID FLUORIDES - THEIR PREPARATION AND USE IN PEPTIDE-SYNTHESIS [J].
BERTHO, JN ;
LOFFET, A ;
PINEL, C ;
REUTHER, F ;
SENNYEY, G .
TETRAHEDRON LETTERS, 1991, 32 (10) :1303-1306
[6]   Thioamide synthesis: Thioacyl-N-phthalimides as thioacylating agents [J].
Brain, CT ;
Hallett, A ;
Ko, SY .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3808-3809
[7]   Optically active 3-amino-2H-azirines as synthons for enantiomerically pure alpha,alpha-disubstituted alpha-amino acids: Syntheses of isovaline synthons and a segment of Trichotoxin A-50 [J].
Bucher, CB ;
Heimgartner, H .
HELVETICA CHIMICA ACTA, 1996, 79 (07) :1903-1915
[8]   ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID FLUORIDES - CONVENIENT NEW PEPTIDE COUPLING REAGENTS APPLICABLE TO THE FMOC/TERT-BUTYL STRATEGY FOR SOLUTION AND SOLID-PHASE SYNTHESES [J].
CARPINO, LA ;
SADATAALAEE, D ;
CHAO, HG ;
DESELMS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9651-9652
[9]   STUDIES ON AMINO-ACIDS AND PEPTIDES .1. SYNTHESIS OF N-BENZYLOXYCARBONYLENDOTHIODIPEPTIDE ESTERS [J].
CLAUSEN, K ;
THORSEN, M ;
LAWESSON, SO .
TETRAHEDRON, 1981, 37 (21) :3635-3639
[10]  
Creagh D.C., 1992, INT TABLES CRYSTALLO, VC, P219