Synthesis of LuxS Inhibitors Targeting Bacterial Cell−Cell Communication
| Autor: | Zhaohui Sunny Zhou, Erin L. Karschner, DonRaphael P. Wynn, Joshua F. Alfaro, Tiao Zhang |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Cell signaling Bacteria biology Chemistry Organic Chemistry Substrate (chemistry) Stereoisomerism biology.organism_classification Biochemistry Bacterial cell structure Substrate Specificity Carbon-Sulfur Lyases Quorum sensing Enzyme Bacterial Proteins Sense (molecular biology) Autoinducer Physical and Theoretical Chemistry Homocysteine |
| Zdroj: | Organic Letters. 6:3043-3046 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol049182i |
| Popis: | [reaction: see text] Quorum sensing is a process by which bacteria sense cell density. This cell-cell communication process is mediated by autoinducers. A cross-species messenger, autoinducer-2 (AI-2) is produced from S-ribosyl-L-homocysteine by the LuxS enzyme. A proposed mechanism for LuxS is an aldose-ketose isomerization of S-ribosylhomocysteine followed by a beta-elimination. We report here the synthesis of two substrate analogues, S-anhydroribosyl-L-homocysteine and S-homoribosyl-L-cysteine, which prevent the initial and final step of the mechanism, respectively. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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