Saponification of esters of chiral α-amino acids anchored through their amine function on solid support

被引：10

作者：

Cantel, S ^{[1
]}

Desgranges, S ^{[1
]}

Martinez, J ^{[1
]}

Fehrentz, JA ^{[1
]}

机构：

[1] Univ Montpellier 1, CNRS, Fac Pharm, LAPP,UMR 5810, F-34093 Montpellier 5, France

来源：

JOURNAL OF PEPTIDE SCIENCE | 2004年 / 10卷 / 06期

关键词：

reverse anchoring; saponification; racemization; solid phase synthesis; Marfey's derivatives;

D O I：

10.1002/psc.561

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Anchoring an alpha-amino acid residue by its amine function onto a solid support is an alternative to develop chemistry on its carboxylic function. This strategy can involve the use of amino-acid esters as precursors of the carboxylic function. A complete study on the Wang-resin was performed to determine the non-racemizing saponification conditions of anchored alpha-amino esters. The use of LiOH, NaOH, NaOSi(Me)(3), various solvents and temperatures were tested for this reaction. After saponification and cleavage from the support, samples were examined through their Marfey's derivatives by reversed phase HPLC to evaluate the percentage of racemization. Copyright (C) 2004 European Peptide Society and John Wiley Sons, Ltd.

引用

页码：326 / 328

页数：3

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