Chemoselective Oxime Reactions in Proteins and Peptides by Using an Optimized Oxime Strategy: The Demise of Levulinic Acid

被引:13
作者
Agten, Stijn M. [1 ]
Suylen, Dennis [1 ]
Ippel, Hans [1 ]
Kokozidou, Maria [1 ]
Tans, Guido [1 ]
van de Vijver, Pieter [1 ]
Koenen, Rory R. [1 ]
Hackeng, Tilman M. [1 ]
机构
[1] Maastricht Univ, Dept Biochem, Cardiovasc Res Inst Maastricht CARIM, NL-6200 MD Maastricht, Netherlands
关键词
bioconjugation; ketones; oximes; peptides; RANTES; CATALYSIS; LIGATION;
D O I
10.1002/cbic.201300598
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
Selecting the right partner faster: In protein chemoselective conjugation, the use of levulinic acid for ketone introduction leads to slow oxime formation and poor yield because of internal cyclization, especially at low concentrations. A mechanism for cyclization is proposed and alternative keto-acids have been tested. These showed faster formation of oximes without side products. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2431 / 2434
页数:4
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