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

TitleChemical synthesis of S-ribosyl-L-homocysteine and activity assay as a LuxS substrate.
Publication TypeJournal Article
Year of Publication2003
AuthorsZhao, G, Wan, W, Mansouri, S, Alfaro, JF, Bassler, BL, Cornell, KA, Zhou, ZSunny
JournalBioorg Med Chem Lett
Volume13
Issue22
Pagination3897-900
Date Published2003 Nov 17
ISSN0960-894X
KeywordsBacillus subtilis, Bacterial Proteins, Carbon-Sulfur Lyases, Homocysteine, Kinetics, Substrate Specificity
Abstract

<p>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.</p>

Alternate JournalBioorg. Med. Chem. Lett.
PubMed ID14592470