Alfaro Joshua F, Zhang Tiao, Wynn DonRaphael P, Karschner Erin L, Zhou Zhaohui Sunny
Department of Chemistry, School of Molecular Biosciences, Center for Integrated Biotechnology, Graduate Program in Pharmacology and Toxicology, Washington State University, Pullman, Washington 99164-4630, USA.
Org Lett. 2004 Sep 2;6(18):3043-6. doi: 10.1021/ol049182i.
[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.
[反应：见正文] 群体感应是细菌感知细胞密度的过程。这种细胞间通讯过程由自诱导物介导。一种跨物种信使，自诱导物-2（AI-2）由LuxS酶从S-核糖基-L-高半胱氨酸产生。关于LuxS的一种推测机制是S-核糖基高半胱氨酸的醛糖-酮糖异构化，随后是β-消除反应。我们在此报告了两种底物类似物，S-脱水核糖基-L-高半胱氨酸和S-高核糖基-L-半胱氨酸的合成，它们分别阻止了该机制的起始步骤和最终步骤。
