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

被引：14

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

页码：5113 / 5119

页数：7

共 73 条

[31] 3-Mercaptopropionic acid-mediated synthesis of peptide and protein thioesters
Kang, Jaskiranjit
Richardson, Jonathan P.
Macmillan, Derek
[J]. CHEMICAL COMMUNICATIONS, 2009, (04) : 407 - 409
[32] Total chemical synthesis of proteins
Kent, Stephen B. H.
[J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (02) : 338 - 351
[33] Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation
Kiick, KL
Saxon, E
Tirrell, DA
Bertozzi, CR
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (01) : 19 - 24
[34] Chemical protein synthesis
Kochendoerfer, GG
Kent, SBH
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (06) : 665 - 671
[35] Chemoselective ligation reactions with proteins, oligosaccharides and cells
Lemieux, GA
Bertozzi, CR
[J]. TRENDS IN BIOTECHNOLOGY, 1998, 16 (12) : 506 - 513
[36] Chk2 Oligomerization Studied by Phosphopeptide Ligation IMPLICATIONS FOR REGULATION AND PHOSPHODEPENDENT INTERACTIONS
Li, Jiejin
Taylor, Ian A.
Lloyd, Janette
Clapperton, Julie A.
Howell, Steven
MacMillan, Derek
Smerdon, Stephen J.
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2008, 283 (51) : 36019 - 36030
[37] Traceless protein splicing utilizing evolved split inteins
Lockless, Steve W.
Muir, Tom W.
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2009, 106 (27) : 10999 - 11004
[38] Rapid synthesis of acyl transfer auxiliaries for cysteine-free native glycopeptide ligation
Macmillan, D
Anderson, DW
[J]. ORGANIC LETTERS, 2004, 6 (25) : 4659 - 4662
[39] Cyanogen bromide cleavage generates fragments suitable for expressed protein and glycoprotein ligation
Macmillan, D
Arham, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9530 - 9531
[40] Modular assembly of glycoproteins: Towards the synthesis of GlyCAM-1 by using expressed protein ligation
Macmillan, D
Bertozzi, CR
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (11) : 1355 - 1359

← 1 2 3 4 5 6 7 8 →