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

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_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Zhao G,Wan W,Mansouri S,Alfaro JF,Bassler BL,Cornell KA,Zhou ZS

doi

10.1016/j.bmcl.2003.09.015

subject

Has Abstract

pub_date

2003-11-17 00:00:00

pages

3897-900

issue

22

eissn

0960-894X

issn

1464-3405

pii

S0960894X03009697

journal_volume

13

pub_type

杂志文章

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