Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents

被引：12

作者：

Alsina, J

Barany, G

Albericio, F

Kates, SA

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

[2] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain

[3] Persept Biosyst Inc, Framingham, MA 01701 USA

来源：

LETTERS IN PEPTIDE SCIENCE | 1999年 / 6卷 / 04期

关键词：

PyAOP; PyBOP; PyBroP; side reactions; solid-phase peptide synthesis;

D O I：

10.1007/BF02443512

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：

Pyrrolidide derivatives are observed as unwanted by-products from slow reactions of activated carboxylates with nucleophilic amines, as mediated by phosphonium salt coupling reagents (PyAOP, PyBOP, PyBroP). This side reaction is attributed to the presence of small amounts (e.g., 0.5%, w/w) of pyrrolidine as a contaminant to commercial phosphonium salts, and does not occur when the reagents are crystallized before their use in coupling reactions.

引用

页码：243 / 245

页数：3

共 9 条

[1]

Albericio F, 1997, METHOD ENZYMOL, V289, P104

[2] Use of onium salt-based coupling reagents in peptide synthesis [J].