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Org Lett. 2004 Sep 2;6(18):3043-6.

Synthesis of LuxS inhibitors targeting bacterial cell-cell communication.

Author information

1
Department of Chemistry, School of Molecular Biosciences, Center for Integrated Biotechnology, Graduate Program in Pharmacology and Toxicology, Washington State University, Pullman, Washington 99164-4630, USA.

Abstract

[reaction: see text] 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 (AI-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.

PMID:
15330583
DOI:
10.1021/ol049182i
[Indexed for MEDLINE]

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