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  • Title: Chemical synthesis of S-ribosyl-L-homocysteine and activity assay as a LuxS substrate.
    Author: Zhao G, Wan W, Mansouri S, Alfaro JF, Bassler BL, Cornell KA, Zhou ZS.
    Journal: Bioorg Med Chem Lett; 2003 Nov 17; 13(22):3897-900. PubMed ID: 14592470.
    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.
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