Access to phosphoproteins and glycoproteins through semi-synthesis, Native Chemical Ligation and N→S acyl transfer

被引：15
作者：
Masania, Jinit [1 ]
Li, Jiejin [2 ]
Smerdon, Stephen J. [2 ]
Macmillan, Derek [1 ]
机构：
[1] UCL, Dept Chem, London WC1H 0AJ, England
[2] MRC Natl Inst Med Res, Div Mol Struct, London NW7 1AA, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 22期
基金：
英国医学研究理事会;
关键词：
CHEMOSELECTIVE LIGATION; EXPRESSED PROTEIN; GLYCOPEPTIDE; PEPTIDE; CHEMISTRY; GLYCOSYLATION; STRATEGIES; MECHANISM; LINKAGE; AZIDES;
D O I：
10.1039/c0ob00363h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Peptide thioesters are important tools for protein synthesis and semi-synthesis through their use in Native Chemical Ligation (NCL). NCL can be employed to assemble site-specifically modified proteins that can help elucidate the mechanisms of biomolecular processes. In this article we explore the compatibility of phosphopeptide synthesis and glycopeptide synthesis with thioester production through N -> S acyl transfer.
引用
收藏
页码：5113 / 5119
页数：7
相关论文
共 73 条
[1]   Combined Approaches to the Synthesis and Study of Glycoproteins [J].
Bernardes, Goncalo J. L. ;
Castagner, Bastien ;
Seeberger, Peter H. .
ACS CHEMICAL BIOLOGY, 2009, 4 (09) :703-713
[2]  
Boltje TJ, 2009, NAT CHEM, V1, P611, DOI [10.1038/NCHEM.399, 10.1038/nchem.399]
[3]   Native chemical ligation using removable Nα-(1-phenyl-2-mercaptoethyl) auxiliaries [J].
Botti, P ;
Carrasco, MR ;
Kent, SBH .
TETRAHEDRON LETTERS, 2001, 42 (10) :1831-1833
[4]   Orthogonal ligation: a three piece assembly of a PNA-peptide-PNA conjugate [J].
Burlina, Fabienne ;
Dixson, David D. ;
Doyle, Robert P. ;
Chassaing, Gerard ;
Boddy, Christopher N. ;
Dawson, Philip ;
Offer, John .
CHEMICAL COMMUNICATIONS, 2008, (24) :2785-2787
[5]   Specific N-terminal protein labelling:: use of FMDV 3Cpro protease and native chemical ligation [J].
Busch, Gillian K. ;
Tate, Edward W. ;
Gaffney, Piers R. J. ;
Rosivatz, Erika ;
Woscholski, Rudiger ;
Leatherbarrow, Robin J. .
CHEMICAL COMMUNICATIONS, 2008, (29) :3369-3371
[6]   Structure and Activation Mechanism of the CHK2 DNA Damage Checkpoint Kinase [J].
Cai, Zhenjian ;
Chehab, Nabil H. ;
Pavletich, Nikola P. .
MOLECULAR CELL, 2009, 35 (06) :818-829
[7]   Peptide chemical ligation inside living cells: In vivo generation of a circular protein domain [J].
Camarero, JA ;
Fushman, D ;
Cowburn, D ;
Muir, TW .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (09) :2479-2484
[8]   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
[9]   Chemical Approaches for Studying Histone Modifications [J].
Chatterjee, Champak ;
Muir, Tom W. .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2010, 285 (15) :11045-11050
[10]   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
12345678