Borinic acid catalysed peptide synthesis

被引：82

作者：

El Dine, Tharwat Mohy ^{[1
]}

Rouden, Jacques ^{[1
]}

Blanchet, Jerome ^{[1
]}

机构：

[1] Univ Caen Normandie, CNRS, ENSICAEN, Lab Chim Mol & Thioorgan, F-14050 Caen, France

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 89期

关键词：

AMIDE BOND FORMATION; CARBOXYLIC-ACIDS; ROOM-TEMPERATURE; DIRECT AMIDATION; COUPLING REAGENTS; BORONIC ACIDS; AMINES; DERIVATIVES; PROTODEBORONATION; DIOLS;

D O I：

10.1039/c5cc06177f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalytic synthesis of peptides is a major challenge in the modern organic chemistry hindered by the well-established use of stoichiometric coupling reagents. Herein, we describe for the first time that borinic acid is able to catalyse this reaction under mild conditions with an improved activity compared to our recently developed thiophene-based boronic acid. This catalyst is particularly efficient for peptide bond synthesis affording dipeptides in good yields without detectable racemization.

引用

页码：16084 / 16087

页数：4

共 36 条

[1] Recent development in peptide coupling reagents [J].

Al-Warhi, Tarfah I. ;

Al-Hazimi, Hassan M. A. ;

El-Faham, Ayman .

JOURNAL OF SAUDI CHEMICAL SOCIETY, 2012, 16 (02) :97-116

[2] Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature [J].

Al-Zoubi, Raed M. ;

Marion, Olivier ;

Hall, Dennis G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2876-2879

[3] Catalytic amidation of unactivated ester derivatives mediated by trifluoroethanol [J].

Caldwell, Nicola ;

Jamieson, Craig ;

Simpson, Iain ;

Watson, Allan J. B. .

CHEMICAL COMMUNICATIONS, 2015, 51 (46) :9495-9498

[4] Borinic Acids: A Neglected Class of Organoboron Compounds for Recognition of Diols in Aqueous Solution [J].

Chudzinski, Michael G. ;

Chi, Yuechuan ;

Taylor, Mark S. .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2011, 64 (11) :1466-1469

[5] Organoboron Acids and Their Derivatives as Catalysts for Organic Synthesis [J].

Dimitrijevic, Elena ;

Taylor, Mark S. .

ACS CATALYSIS, 2013, 3 (05) :945-962

[6] Catalytic Chemical Amide Synthesis at Room Temperature: One More Step Toward Peptide Synthesis [J].

El Dine, Tharwat Mohy ;

Erb, William ;

Berhault, Yohann ;

Rouden, Jacques ;

Blanchet, Jerome .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09) :4532-4544

[7] Peptide Coupling Reagents, More than a Letter Soup [J].

El-Faham, Ayman ;

Albericio, Fernando .

CHEMICAL REVIEWS, 2011, 111 (11) :6557-6602

[8] Direct Amidation of Carboxylic Acids Catalyzed by ortho-Iodo Arylboronic Acids: Catalyst Optimization, Scope, and Preliminary Mechanistic Study Supporting a Peculiar Halogen Acceleration Effect [J].

Gernigon, Nicolas ;

Al-Zoubi, Raed M. ;

Hall, Dennis G. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) :8386-8400

[9]

Gu L., 2014, CHEM COMMUN, V50, P7017

[10] 3,4,5-trifluorobenzeneboronic acid as an extremely active amidation catalyst [J].

Ishihara, K ;

Ohara, S ;

Yamamoto, H .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4196-4197

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