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 journalArticle

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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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