Peptide Ligation-Desulfurization Chemistry at Arginine

被引:79
作者
Malins, Lara R. [1 ]
Cergol, Katie M. [1 ]
Payne, Richard J. [1 ]
机构
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
基金
澳大利亚研究理事会;
关键词
arginine; desulfurization; glycopeptides; ligation; peptides; NATIVE CHEMICAL LIGATION; KINETICALLY CONTROLLED LIGATION; HUMAN PARATHYROID-HORMONE; PROTEIN-SYNTHESIS; PROLINE LIGATION; ERYTHROPOIETIN; GLYCOPEPTIDES; CYSTEINE; BETA; DESELENIZATION;
D O I
10.1002/cbic.201300049
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
The utility of a new beta-thiol arginine building block in ligation-desulfurization chemistry has been demonstrated through reactions and kinetic studies with a range of peptide thioesters. Application of the method is highlighted by a one-pot, kinetically controlled, rapid ligation to generate a 7 kDa MUC1 glycopeptide.
引用
收藏
页码:559 / 563
页数:5
相关论文
共 63 条
[1]  
Ajish KumarK.S., 2009, Angewandte Chemie, V121, P8234, DOI DOI 10.1002/ANGE.200902936
[2]  
[Anonymous], 2011, ANGEW CHEM-GER EDIT
[3]  
[Anonymous], 2011, ANGEW CHEM
[4]  
[Anonymous], ANGEW CHEM INT ED EN
[5]  
Bang D., 2006, ANGEW CHEM, V118, P4089
[6]   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
[7]  
Bavikar S. N., 2012, ANGEW CHEM, V124, P782
[8]   Chemical Synthesis of Ubiquitinated Peptides with Varying Lengths and Types of Ubiquitin Chains to Explore the Activity of Deubiquitinases [J].
Bavikar, Sudhir N. ;
Spasser, Liat ;
Haj-Yahya, Mahmood ;
Karthikeyan, Subramanian Vedhanarayanan ;
Moyal, Tal ;
Kumar, K. S. Ajish ;
Brik, Ashraf .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) :758-763
[9]   Synthetic glycopeptides from the mucin family as potential tools in cancer immunotherapy [J].
Becker, Torsten ;
Dziadek, Sebastian ;
Wittrock, Sven ;
Kunz, Horst .
CURRENT CANCER DRUG TARGETS, 2006, 6 (06) :491-517
[10]  
Botti P., 2006, [No title captured], Patent No. [WO2006133962, 2006133962, WO 2006/133962]