In situ thioester formation for protein ligation using α-methylcysteine

被引：41

作者：

Burlina, Fabienne ^{[1
,2
,3
]}

Papageorgiou, George ^{[4
]}

Morris, Caroline ^{[4
]}

White, Peter D. ^{[5
]}

Offer, John ^{[4
]}

机构：

[1] Univ Paris 06, UMR 7203, Lab BioMol, F-75005 Paris, France

[2] CNRS, UMR 7203, Lab BioMol, F-75700 Paris, France

[3] ENS, Dept Chim, UMR 7203, Lab BioMol, F-75230 Paris 05, France

[4] Natl Inst Med Res, London NW7 1AA, England

[5] Merck Chem, Beeston NG9 2JR, Notts, England

来源：

CHEMICAL SCIENCE | 2014年 / 5卷 / 02期

关键词：

NATIVE CHEMICAL LIGATION; PEPTIDE-BOND; EFFICIENT SYNTHESIS; CYSTEINE PEPTIDES; THIOL CAPTURE; AMIDE BONDS; SIDE-CHAIN; HYDROLYSIS; SEMISYNTHESIS; CHEMISTRY;

D O I：

10.1039/c3sc52140k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The progress of total chemical protein synthesis has been hampered by difficulties in preparing peptide thioesters by standard Fmoc peptide synthesis. The amino acid, alpha-methylcysteine, sited at the C-terminus of a peptide can substitute for a thioester in peptide ligation reactions. C-terminal alpha-methylcysteine is fully compatible with Fmoc peptide synthesis and its use in ligation is very simple and robust. Its potential is demonstrated with the synthesis of model proteins.

引用

页码：766 / 770

页数：5

共 60 条

[1] An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation [J].

Blanco-Canosa, Juan B. ;

Dawson, Philip E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (36) :6851-6855

[2] Native chemical ligation through in situ O to S acyl shift [J].

Botti, P ;

Villain, M ;

Manganiello, S ;

Gaertner, H .

ORGANIC LETTERS, 2004, 6 (26) :4861-4864

[3]

BRENNER M., 1967, P1

[4] Direct measurement of the uncatalyzed rate of hydrolysis of a peptide bond [J].

Bryant, RAR ;

Hansen, DE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (23) :5498-5499

[5] Simplifying native chemical ligation with an N-acylsulfonamide linker [J].

Burlina, Fabienne ;

Morris, Caroline ;

Behrendt, Raymond ;

White, Peter ;

Offer, John .

CHEMICAL COMMUNICATIONS, 2012, 48 (20) :2579-2581

[6] A NOVEL 4-AMINOBENZYL ESTER-BASED CARBOXY-PROTECTING GROUP FOR SYNTHESIS OF ATYPICAL PEPTIDES BY FMOC-BU(T) SOLID-PHASE CHEMISTRY [J].

CHAN, WC ;

BYCROFT, BW ;

EVANS, DJ ;

WHITE, PD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) :2209-2210

[7]

Clayden J, 2002, EUR J ORG CHEM, V2002, P3558

[8] ORGANIC CHEMISTRY Stabilizers cause instability [J].

Clayden, Jonathan .

NATURE, 2012, 481 (7381) :274-275

[9] Making Ends Meet: Chemically Mediated Circularization of Recombinant Proteins [J].

Cowper, Ben ;

Craik, David J. ;

Macmillan, Derek .

CHEMBIOCHEM, 2013, 14 (07) :809-812

[10] SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].

DAWSON, PE ;

MUIR, TW ;

CLARKLEWIS, I ;

KENT, SBH .

SCIENCE, 1994, 266 (5186) :776-779

← 1 2 3 4 5 6 →