Direct on-resin synthesis of peptide-αthiophenylesters for use in native chemical ligation

被引:37
作者
Bang, D [1 ]
Pentelute, BL
Gates, ZP
Kent, SB
机构
[1] Univ Chicago, Dept Chem, Inst Biophys Dynam, Chicago, IL 60637 USA
[2] Univ Chicago, Dept Biochem & Mol Biol, Chicago, IL 60637 USA
关键词
D O I
10.1021/ol052811j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A peptide-(alpha)thiophenylester is a key reactant in native chemical ligation. Preformation of the peptide-(alpha)thiophenylester could be useful for enhancing the ligation reaction. We report the direct on-resin preparation of preformed peptide-(alpha)thiophenylesters using a simple and efficient method. The peptide-(alpha)thiophenylester reacted extremely rapidly with a Cys-peptide when compared to the peptide-(alpha)thioalkylester.
引用
收藏
页码:1049 / 1052
页数:4
相关论文
共 7 条
[1]  
BANG DD, UNPUB
[2]   SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].
DAWSON, PE ;
MUIR, TW ;
CLARKLEWIS, I ;
KENT, SBH .
SCIENCE, 1994, 266 (5186) :776-779
[3]   Modulation of reactivity in native chemical ligation through the use of thiol additives [J].
Dawson, PE ;
Churchill, MJ ;
Ghadiri, MR ;
Kent, SBH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) :4325-4329
[4]   Synthesis of native proteins by chemical ligation [J].
Dawson, PE ;
Kent, SBH .
ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 :923-960
[5]   CARBOXYL-CATALYZED INTRAMOLECULAR AMINOLYSIS - SIDE REACTION IN SOLID-PHASE PEPTIDE SYNTHESIS [J].
GISIN, BF ;
MERRIFIELD, RB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (09) :3102-+
[6]   Protein synthesis by native chemical ligation: Expanded scope by using straightforward methodology [J].
Hackeng, TM ;
Griffin, JH ;
Dawson, PE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (18) :10068-10073
[7]  
SCHNOLZER M, 1992, INT J PEPT PROT RES, V40, P180