Synthesis of constrained helical peptides by thioether ligation: application to analogs of gp41

被引：83

作者：

Brunel, FM ^{[1
]}

Dawson, PE ^{[1
]}

机构：

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

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 20期

关键词：

D O I：

10.1039/b419015g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present a straightforward and high yielding method to synthesize constrained helical peptides via thioether ligation; this method represents an attractive alternative to the formation of lactam bridge constraints to induce helicity in peptides.

引用

页码：2552 / 2554

页数：3

共 21 条

[1] Comprehensive cross-clade neutralization analysis of a panel of anti-human immunodeficiency virus type 1 monoclonal antibodies [J].

Binley, JA ;

Wrin, T ;

Korber, B ;

Zwick, MB ;

Wang, M ;

Chappey, C ;

Stiegler, G ;

Kunert, R ;

Zolla-Pazner, S ;

Katinger, H ;

Petropoulos, CJ ;

Burton, DR .

JOURNAL OF VIROLOGY, 2004, 78 (23) :13232-13252

[2] Ring-closing metathesis of olefinic peptides: Design, synthesis, and structural characterization of macrocyclic helical peptides [J].

Blackwell, HE ;

Sadowsky, JD ;

Howard, RJ ;

Sampson, JN ;

Chao, JA ;

Steinmetz, WE ;

O'Leary, DJ ;

Grubbs, RH .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5291-5302

[3]

Blackwell HE, 1998, ANGEW CHEM INT EDIT, V37, P3281, DOI 10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO

[4]

2-V

[5] Cyclic peptides from linear unprotected peptide precursors through thiazolidine formation [J].

Botti, P ;

Pallin, TD ;

Tam, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (42) :10018-10024

[6]

CARDOSO RMF, IN PRESS IMMUNITY

[7] Core structure of gp41 from the HIV envelope glycoprotein [J].

Chan, DC ;

Fass, D ;

Berger, JM ;

Kim, PS .

CELL, 1997, 89 (02) :263-273

[8]

CREIGHTON TE, 1984, PROTEINS STRUCTURES, P182

[9] Synthesis of native proteins by chemical ligation [J].

Dawson, PE ;

Kent, SBH .

ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 :923-960

[10]

DOVALSANTOS E, HOUBENWEYL METHODS C, V22, P759

← 1 2 3 →