Nα-2-mercaptobenzylamine-assisted chemical ligation

被引：88

作者：

Offer, J

Dawson, PE ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Cell Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[3] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 01期

关键词：

D O I：

10.1021/ol991184t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The selective formation of an amide bond in the presence of unprotected functional groups is a challenging problem of peptide chemistry. A 2-mercaptobenzyl group tethered at the N-terminus of model peptides was observed to facilitate amide bond formation when a peptide thioester was added under mild aqueous conditions.

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页码：23 / 26

页数：4

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共 27 条

[1] Novel solid-phase reagents for facile formation of intramolecular disulfide bridges in peptides under mild conditions [J].

Annis, I ;

Chen, L ;

Barany, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) :7226-7238

[2]

BRENNER M., 1967, P1

[3] Chemical protein synthesis by solid phase ligation of unprotected peptide segments [J].

Canne, LE ;

Botti, P ;

Simon, RJ ;

Chen, YJ ;

Dennis, EA ;

Kent, SBH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (38) :8720-8727

[4] Extending the applicability of native chemical ligation [J].

Canne, LE ;

Bark, SJ ;

Kent, SBH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) :5891-5896

[5] CONSTITUTION OF N-SUBSTITUTED 2-(IMINOMETHYL)BENZENETHIOLS (ORTHO-MERCAPTOBENZALDIMINES) [J].

CORRIGAN, MF ;

RAE, ID ;

WEST, BO .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (03) :587-594

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

DAWSON, PE ;

MUIR, TW ;

CLARKLEWIS, I ;

KENT, SBH .

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

[7] Modulation of reactivity in native chemical ligation through the use of thiol additives [J].

Dawson, PE ;

Churchill, MJ ;

Ghadiri, MR ;

Kent, SBH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) :4325-4329

[8] Incorporation of 2-hydroxy-4-methoxybenzyl protection during peptide synthesis via reductive alkylation on the solid phase [J].

Ede, NJ ;

Ang, KH ;

James, IW ;

Bray, AM .

TETRAHEDRON LETTERS, 1996, 37 (50) :9097-9100

[9] A NOVEL THIOETHER LINKER - CHEMICAL SYNTHESIS OF A HIV-1 PROTEASE ANALOG BY THIOETHER LIGATION [J].

ENGLEBRETSEN, DR ;

GARNHAM, BG ;

BERGMAN, DA ;

ALEWOOD, PF .

TETRAHEDRON LETTERS, 1995, 36 (48) :8871-8874

[10] CONSTRUCTION OF PROTEIN ANALOGS BY SITE-SPECIFIC CONDENSATION OF UNPROTECTED FRAGMENTS [J].

GAERTNER, HF ;

ROSE, K ;

COTTON, R ;

TIMMS, D ;

CAMBLE, R ;

OFFORD, RE .

BIOCONJUGATE CHEMISTRY, 1992, 3 (03) :262-268