Cysteine Promoted C-Terminal Hydrazinolysis of Native Peptides and Proteins

被引:62
作者
Adams, Anna L. [1 ]
Cowper, Ben [1 ]
Morgan, Rachel E. [1 ]
Premdjee, Bhavesh [1 ]
Caddick, Stephen [1 ]
Macmillan, Derek [1 ]
机构
[1] UCL, Dept Chem, London WC1H 0AJ, England
基金
英国工程与自然科学研究理事会; 英国惠康基金;
关键词
acyl transfer; erythropoietin; hydrazides; native chemical ligation; peptides; ACTIVE ESTER CONDENSATION; CHEMICAL-SYNTHESIS; SITE; ERYTHROPOIETIN; HYDRAZIDES; EFFICIENT; LIGATION;
D O I
10.1002/anie.201304997
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tagging the terminus: N→S acyl transfer in native peptides and proteins can be reliably intercepted with hydrazine. The method allows selective labeling and ligation, without recourse to the use of protein-splicing elements. NCL=native chemical ligation. © 2013 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:13062 / 13066
页数:5
相关论文
共 32 条
[1]  
ACKRILL T, 2010, PEPT SCI, V94, P495
[2]  
Ajish KumarK.S., 2009, Angewandte Chemie, V121, P8234, DOI DOI 10.1002/ANGE.200902936
[3]  
[Anonymous], 2011, ANGEW CHEM
[4]   Probing the stability of nonglycosylated wild-type erythropoietin protein via reiterative alanine ligations [J].
Brailsford, John A. ;
Danishefsky, Samuel J. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2012, 109 (19) :7196-7201
[5]  
Chatterjee C., 2007, ANGEW CHEM, V119, P2872
[6]   Auxiliary-mediated site-specific peptide ubiquitylation [J].
Chatterjee, Champak ;
McGinty, Robert K. ;
Pellois, Jean-Philippe ;
Muir, Tom W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (16) :2814-2818
[7]   NMR structure of human erythropoietin and a comparison with its receptor bound conformation [J].
Cheetham, JC ;
Smith, DM ;
Aoki, KH ;
Stevenson, JL ;
Hoeffel, TJ ;
Syed, RS ;
Egrie, J ;
Harvey, TS .
NATURE STRUCTURAL BIOLOGY, 1998, 5 (10) :861-866
[8]   Mapping of the active site of recombinant human erythropoietin [J].
Elliott, S ;
Lorenzini, T ;
Chang, D ;
Barzilay, J ;
Delorme, E .
BLOOD, 1997, 89 (02) :493-502
[9]  
Fang G., 2011, ANGEW CHEM, V123, P7787, DOI DOI 10.1002/ANGE.201100996
[10]   Protein Chemical Synthesis by Ligation of Peptide Hydrazides [J].
Fang, Ge-Min ;
Li, Yi-Ming ;
Shen, Fei ;
Huang, Yi-Chao ;
Li, Jia-Bin ;
Lin, Yun ;
Cui, Hong-Kui ;
Liu, Lei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7645-7649