Phosphate-assisted peptide ligation

被引:24
作者
Thomas, Gemma L. [1 ]
Payne, Richard J. [1 ]
机构
[1] Univ Sydney, Sch Biol Sci, Sydney, NSW 2006, Australia
关键词
NATIVE CHEMICAL LIGATION; CYSTEINE-FREE PEPTIDE; GLYCOPEPTIDE SYNTHESIS; STAUDINGER LIGATION; STRATEGIES; PHOSPHOPEPTIDES; AMINOACYLATION; THIOESTER; PROTEINS; VALINE;
D O I
10.1039/b906492c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel ligation method for the synthesis of phosphopeptides and peptides is described, which utilises the inherent reactivity of a peptide bearing an N-terminal phosphoserine or phosphothreonine residue to facilitate amide bond formation with a range of C-terminal peptide thioesters.
引用
收藏
页码:4260 / 4262
页数:3
相关论文
共 30 条
[1]  
Aimoto S, 1999, BIOPOLYMERS, V51, P247, DOI 10.1002/(SICI)1097-0282(1999)51:4<247::AID-BIP2>3.0.CO
[2]  
2-W
[3]   Synthesis of phosphopeptides in the fmoc mode [J].
Attard, Troy J. ;
O'Brien-Simpson, Neil ;
Reynolds, Eric C. .
INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2007, 13 (04) :447-468
[4]   Sugar-assisted glycopeptide ligation [J].
Brik, A ;
Yang, YY ;
Ficht, S ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5626-5627
[5]   Biomimetic monoacylation of diols in water. Lanthanide-promoted reactions of methyl benzoyl phosphate [J].
Cameron, LL ;
Wang, SC ;
Kluger, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10721-10726
[6]   Development of efficient methods for accomplishing cysteine-free peptide and glycopeptide coupling [J].
Chen, Gong ;
Wan, Qian ;
Tan, Zhongping ;
Kan, Cindy ;
Hua, Zihao ;
Ranganathan, Krishnakumar ;
Danishefsky, Samuel J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) :7383-7387
[7]   Native Chemical Ligation at Valine: A Contribution to Peptide and Glycopeptide Synthesis [J].
Chen, Jin ;
Wan, Qian ;
Yuan, Yu ;
Zhu, Jianglong ;
Danishefsky, Samuel J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8521-8524
[8]   Native chemical ligation at phenylalanine [J].
Crich, David ;
Banerjee, Abhisek .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (33) :10064-+
[9]   Synthesis of glycoproteins [J].
Davis, BG .
CHEMICAL REVIEWS, 2002, 102 (02) :579-601
[10]   SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].
DAWSON, PE ;
MUIR, TW ;
CLARKLEWIS, I ;
KENT, SBH .
SCIENCE, 1994, 266 (5186) :776-779