Synthesis of LuxS inhibitors targeting bacterial cell-cell communication

被引：71

作者：

Alfaro, JF ^{[1
]}

Zhang, T

Wynn, DP

Karschner, EL

Zhou, ZS

机构：

[1] Washington State Univ, Dept Chem, Pullman, WA 99164 USA

[2] Washington State Univ, Sch Mol Biosci, Pullman, WA 99164 USA

[3] Washington State Univ, Ctr Integrated Biotechnol, Pullman, WA 99164 USA

[4] Washington State Univ, Grad Program Pharmacol & Toxicol, Pullman, WA 99164 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 18期

关键词：

D O I：

10.1021/ol049182i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quorum sensing is a process by which bacteria sense cell density. This cell-cell communication process is mediated by autoinducers. A cross-species messenger, autoinducer-2 (Al-2) is produced from S-ribosyl-L-homocysteine by the LuxS enzyme. A proposed mechanism for LuxS is an aldose-ketose isomerization of S-ribosylhomocysteine followed by a beta-elimination. We report here the synthesis of two substrate analogues, S-anhydroribosyl-L-homocysteine and S-homoribosyl-L-cysteine, which prevent the initial and final step of the mechanism, respectively.

引用

页码：3043 / 3046

页数：4

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