N-terminal α-amino group modification of peptides by an oxime formation-exchange reaction sequence

被引：35
作者：
Kung, Karen Ka-Yan
Wong, Kong-Fan
Leung, King-Chi
Wong, Man-Kin [1 ]
机构：
[1] Hong Kong Polytech Univ, State Key Lab Chirosci, Hong Kong, Hong Kong, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 61期
关键词：
BIOMIMETIC TRANSAMINATION REACTION; PROTEIN MODIFICATION; AQUEOUS-MEDIUM; CHEMICAL-SYNTHESIS; POSTTRANSLATIONAL MODIFICATIONS; SECONDARY-AMINES; AMIDE SYNTHESIS; LIGATION; IMMOBILIZATION; OXIDATION;
D O I：
10.1039/c3cc42261e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A site-specific and efficient method for N-terminal modification of peptides using oxone for selective oxidation of N-terminal alpha-amino groups of peptides to oximes followed by transoximation with O-substituted hydroxylamines has been developed.
引用
收藏
页码：6888 / 6890
页数：3
相关论文
共 41 条
[1]   A comparative study of bioorthogonal reactions with azides [J].
Agard, Nicholas J. ;
Baskin, Jeremy M. ;
Prescher, Jennifer A. ;
Lo, Anderson ;
Bertozzi, Carolyn R. .
ACS CHEMICAL BIOLOGY, 2006, 1 (10) :644-648
[2]   Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction [J].
Alam, Jenefer ;
Keller, Thomas H. ;
Loh, Teck-Peng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (28) :9546-9548
[3]  
Aslam M., 1998, Bioconjugation: Protein coupling techniques for the biomedical sciences
[4]   Kinetically controlled ligation for the convergent chemical synthesis of proteins [J].
Bang, Duhee ;
Pentelute, Brad L. ;
Kent, Stephen B. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3985-3988
[5]   Protein Chemical Modification on Endogenous Amino Acids [J].
Basle, Emmanuel ;
Joubert, Nicolas ;
Pucheault, Mathieu .
CHEMISTRY & BIOLOGY, 2010, 17 (03) :213-227
[6]   Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids [J].
Bode, JW ;
Fox, RM ;
Baucom, KD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) :1248-1252
[7]   Chemoselective modification of proteins: hitting the target [J].
Carrico, Isaac S. .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (07) :1423-1431
[8]   Gold-mediated selective cysteine modification of peptides using allenes [J].
Chan, Anna On-Yee ;
Tsai, Johnson Lui-Lui ;
Lo, Vanessa Kar-Yan ;
Li, Gai-Li ;
Wong, Man-Kin ;
Che, Chi-Ming .
CHEMICAL COMMUNICATIONS, 2013, 49 (14) :1428-1430
[9]   Modification of N-Terminal α-Amino Groups of Peptides and Proteins Using Ketenes [J].
Chan, Anna On-Yee ;
Ho, Chi-Ming ;
Chong, Hiu-Chi ;
Leung, Yun-Chung ;
Huang, Jie-Sheng ;
Wong, Man-Kin ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) :2589-2598
[10]   Oxidative amide synthesis and N-terminal α-amino group ligation of peptides in aqueous medium [J].
Chan, Wing-Kei ;
Ho, Chi-Ming ;
Wong, Man-Kin ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14796-14797
12345