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

Publication Year
2003

Type

Journal Article
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.

Journal
Bioorg Med Chem Lett
Volume
13
Issue
22
Pages
3897-900
Date Published
2003 Nov 17
ISSN Number
0960-894X
Alternate Journal
Bioorg Med Chem Lett
PMID
14592470