A new ligation method for N-terminal tryptophan-containing peptides using the Pictet-Spengler reaction

被引：66

作者：

Li, XF

Zhang, LS ^{[1
]}

Hall, SE

Tam, JP

机构：

[1] Eli Lilly & Co, Div A, Sphinx Pharmaceut, Cambridge, MA 02139 USA

[2] Vanderbilt Univ, Dept Microbiol & Immunol, Nashville, TN 37232 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(00)00592-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Application of a carbon-carbon bond forming reaction for ligating unprotected peptides in acetic acid is described based on a Pictet-Spengler condensation. The peptide segments include a peptide with a Trp at the N-terminal and another with a C-terminal aldehyde, which can be generated through a new cyclic acetal resin. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：4069 / 4073

页数：5

相关论文

共 26 条

[1] 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

[2] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

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

DAWSON, PE ;

MUIR, TW ;

CLARKLEWIS, I ;

KENT, SBH .

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

[4] 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

[5] The in vitro ligation of bacterially expressed proteins using an intein from Methanobacterium thermoautotrophicum [J].

Evans, TC ;

Benner, J ;

Xu, MQ .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (07) :3923-3926

[6]

FRECHET JM, 1971, J AM CHEM SOC, V93, P492

[7] SOLID-PHASE SYNTHESIS OF 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES - IMPLICATIONS FOR COMBINATORIAL CHEMISTRY [J].

KALJUSTE, K ;

UNDEN, A .

TETRAHEDRON LETTERS, 1995, 36 (50) :9211-9214

[8] Total chemical synthesis of the integral membrane protein influenza A virus M2: Role of its C-terminal domain in tetramer assembly [J].

Kochendoerfer, GG ;

Salom, D ;

Lear, JD ;

Wilk-Orescan, R ;

Kent, SBH ;

DeGrado, WF .

BIOCHEMISTRY, 1999, 38 (37) :11905-11913

[9] PEPTIDE SEGMENT LIGATION STRATEGY WITHOUT USE OF PROTECTING GROUPS [J].

LIU, CF ;

TAM, JP .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (14) :6584-6588

[10] Application of the Pictet-Spengler reaction in combinatorial chemistry. [J].

Mayer, JP ;

BankaitisDavis, D ;

Zhang, JW ;

Beaton, G ;

Bjergarde, K ;

Andersen, CM ;

Goodman, BA ;

Herrera, CJ .

TETRAHEDRON LETTERS, 1996, 37 (32) :5633-5636