Synthesis of LuxS Inhibitors Targeting Bacterial Cell−Cell Communication
- 4 August 2004
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (18) , 3043-3046
- https://doi.org/10.1021/ol049182i
Abstract
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 β-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.Keywords
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