Chemoselective peptide cyclization by traceless Staudinger ligation

被引：90
|
作者：
Kleineweischede, Rolf [1 ]
Hackenberger, Christian P. R. [1 ]
机构：
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 32期
关键词：
chemoselectivity; cyclization; peptides; protecting groups; protein design;
D O I：
10.1002/anie.200801514
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Two birds with one stone! An intramolecular traceless Staudinger ligation was employed to synthesize cyclic peptides. The final amide bond formation was induced by deprotection of the azidopeptide phosphinothioesters. Treatment with trifluoroacetic acid (TFA) results in the simultaneous removal of the borane along with the protecting groups on the peptide side chains, and chemoselective amide bond cyclization ensues. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：5984 / 5988
页数：5
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