Chemical synthesis of S-ribosyl-L-homocysteine and activity assay as a LuxS substrate

Gang Zhao, Wei Wan, Shahrzad Mansouri, Joshua F. Alfaro, Bonnie L. Bassler, Kenneth A. Cornell, Zhaohui Sunny Zhou

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

Bacterial quorum sensing is mediated by autoinducers, small signaling molecules generated by bacteria. It has been proposed that the LuxS enzyme converts S-ribosyl-L-homocysteine to 4,5-dihydroxy-2,3-pentanedione, the precursor of autoinducer 2 (AI-2). We report here a chemical synthesis of S-ribosyl-L-homocysteine and its analogue using Mitsunobu coupling. Chemically synthesized ribosylhomocysteine has been confirmed as a substrate for LuxS in both an enzyme assay and a whole cell quorum sensing assay. The chemical entities of products from the LuxS reaction were also established. Several ribosylhomocysteine analogues have been tested as LuxS inhibitors.

Original languageEnglish
Pages (from-to)3897-3900
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume13
Issue number22
DOIs
StatePublished - 17 Nov 2003

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