ACTIVATION OF N,N-BIS(ALKOXYCARBONYL) AMINO-ACIDS - SYNTHESIS OF N-ALKOXYCARBONYL AMINO-ACID N-CARBOXYANHYDRIDES AND N,N-DIALKOXYCARBONYL AMINO-ACID FLUORIDES, AND THE BEHAVIOR OF THESE AMINO-ACID DERIVATIVES

被引:23
作者
SAVRDA, J [1 ]
CHERTANOVA, L [1 ]
WAKSELMAN, M [1 ]
机构
[1] INST CHIM SUBST NAT,CNRS,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/S0040-4020(01)80689-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Series of Boc- and Cbz-NCAs (2), and of N,N-bis(alkoxycarbonyl) amino acid fluorides U(2)AAFs (3) have been prepared by activation of N,N-bis-Boc- and N-Cbz,N-Boc-alpha-amino acids (1) with the Vilsmeier reagent or cyanuric fluoride. The absence of epimerization of 2 and 3 during both their formation and their coupling under standard conditions of peptide synthesis had been demonstrated by optical purity Young's tests. In other activated derivatives of bis-urethane protected activated amino acids, the exchangeability of the alpha-H is shown by the considerable racemization of Boc(2)Phe-OSu (8) in the presence of base, and by the formation of a Dakin-West type product 11 from the dipeptide Boc(2)Phe-Leu-OBn.
引用
收藏
页码:5309 / 5322
页数:14
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