In situ generation of Fmoc-amino acid chlorides using bis(trichloromethyl) carbonate and its utilization for difficult couplings in solid-phase peptide synthesis

被引：135

作者：

Falb, E

Yechezkel, T

Salitra, Y

Gilon, C ^{[1
]}

机构：

[1] Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel

[2] Peptor Ltd, IL-76326 Rehovot, Israel

来源：

JOURNAL OF PEPTIDE RESEARCH | 1999年 / 53卷 / 05期

关键词：

acid chlorides; backbone cyclic peptides; bis(trichloromethyl)carbonate; difficult couplings; N-alkylated amino acids; solid-phase peptide synthesis;

D O I：

10.1034/j.1399-3011.1999.00049.x

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

This paper reports procedures for the straightforward in situ generation of Fmoc-amino acid chlorides using bis(trichloromethyl)carbonate (BTC) and their utilization for difficult couplings during solid-phase peptide synthesis. The BTC-mediated coupling of all Fmoc-protected proteinogenic amino acids to a large variety of N-alkylated amino acid-peptidyl-resin was studied. The majority of the couplings proceeded with quantitative conversion and without racemization. The utilization of ETC-mediated coupling for facile solid-phase synthesis of backbone cyclic peptides is presented.

引用

页码：507 / 517

页数：11

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