An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

被引：40

作者：

Ascenso, Osvaldo S. ^{[1
,2
]}

Marques, Joao C. ^{[2
]}

Santos, Ana Rita ^{[1
,2
]}

Xavier, Karina B. ^{[1
,2
]}

Rita Ventura, M. ^{[1
]}

Maycock, Christopher D. ^{[1
,3
]}

机构：

[1] Univ Nova Lisboa, Inst Tecnol Quim & Biol, P-2780901 Oeiras, Portugal

[2] Inst Gulbenkian Ciencias, P-2781901 Oeiras, Portugal

[3] Univ Lisbon, Fac Ciencias, Dept Quim & Bioquim, P-1749016 Lisbon, Portugal

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2011年 / 19卷 / 03期

关键词：

DPD; AI-2; Quorum sensing; Enantioselective reduction; C-13-DPD; SALMONELLA-TYPHIMURIUM; VIBRIO-HARVEYI; LUXS; COMMUNICATION; VALIDATION; FAMILY; DPD;

D O I：

10.1016/j.bmc.2010.12.036

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1236 / 1241

页数：6

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