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本文引用的文献

1
Probing the catalytic mechanism of S-ribosylhomocysteinase (LuxS) with catalytic intermediates and substrate analogues.利用催化中间体和底物类似物探究S-核糖基高半胱氨酸酶（LuxS）的催化机制。
J Am Chem Soc. 2009 Jan 28;131(3):1243-50. doi: 10.1021/ja808206w.
2
An unexpected switch in the modulation of AI-2-based quorum sensing discovered through synthetic 4,5-dihydroxy-2,3-pentanedione analogues.通过合成4,5-二羟基-2,3-戊二酮类似物发现基于AI-2群体感应调控中的意外转变。
J Am Chem Soc. 2008 Jul 23;130(29):9200-1. doi: 10.1021/ja802353j. Epub 2008 Jun 25.
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S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit.碳-5和硫原子被乙烯基或（氟）乙烯基单元取代的S-核糖基高半胱氨酸类似物。
Bioorg Med Chem. 2008 May 1;16(9):5090-102. doi: 10.1016/j.bmc.2008.03.028. Epub 2008 Mar 14.
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An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents.作为潜在抗肿瘤和/或抗病毒药物的胸腺嘧啶、尿嘧啶和5-氟尿嘧啶的3-氟-5-硫代木糖呋喃糖基核苷的高效合成。
Bioorg Med Chem. 2007 May 1;15(9):3241-7. doi: 10.1016/j.bmc.2007.02.031. Epub 2007 Feb 20.
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Ac2-DPD, the bis-(O)-acetylated derivative of 4,5-dihydroxy-2,3-pentanedione (DPD) is a convenient stable precursor of bacterial quorum sensing autoinducer AI-2.Ac2-DPD，即4,5-二羟基-2,3-戊二酮（DPD）的双（O）-乙酰化衍生物，是细菌群体感应自诱导物AI-2的一种便捷稳定的前体。
Bioorg Med Chem Lett. 2007 Mar 1;17(5):1428-31. doi: 10.1016/j.bmcl.2006.11.076. Epub 2006 Dec 2.
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Functional analysis of luxS in the probiotic strain Lactobacillus rhamnosus GG reveals a central metabolic role important for growth and biofilm formation.益生菌鼠李糖乳杆菌GG中luxS的功能分析揭示了其在生长和生物膜形成中起重要作用的核心代谢功能。
J Bacteriol. 2007 Feb;189(3):860-71. doi: 10.1128/JB.01394-06. Epub 2006 Nov 10.
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Structure and inhibition of a quorum sensing target from Streptococcus pneumoniae.肺炎链球菌群体感应靶点的结构与抑制作用
Biochemistry. 2006 Oct 31;45(43):12929-41. doi: 10.1021/bi061184i.
8
Catalytic mechanism of S-ribosylhomocysteinase: ionization state of active-site residues.S-核糖基高半胱氨酸酶的催化机制：活性位点残基的电离状态
Biochemistry. 2006 Oct 10;45(40):12195-203. doi: 10.1021/bi061434v.
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Design and synthesis of substrate and intermediate analogue inhibitors of S-ribosylhomocysteinase.S-核糖基高半胱氨酸酶底物及中间体类似物抑制剂的设计与合成
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Bacterially speaking.从细菌的角度来说。
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核糖基C-3位修饰的底物类似物对S-核糖基高半胱氨酸酶（LuxS）的抑制作用。

Inhibition of S-ribosylhomocysteinase (LuxS) by substrate analogues modified at the ribosyl C-3 position.

作者信息

Wnuk Stanislaw F, Robert Jenay, Sobczak Adam J, Meyers Brandon P, Malladi Venkata L A, Zhu Jinge, Gopishetty Bhaskar, Pei Dehua

机构信息

Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA.

出版信息

Bioorg Med Chem. 2009 Sep 15;17(18):6699-706. doi: 10.1016/j.bmc.2009.07.057. Epub 2009 Jul 26.

DOI:10.1016/j.bmc.2009.07.057
PMID:19682914
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2765115/
Abstract

S-ribosylhomocysteinase (LuxS) catalyzes the cleavage of the thioether bond of S-ribosylhomocysteine (SRH) to produce homocysteine and 4,5-dihydroxy-2,3-pentanedione (DPD), which is the precursor of type 2 autoinducer for bacterial cell-cell communication. In this work, we have synthesized several SRH analogues modified at the ribose C3 position as potential inhibitors of LuxS. While removal or methylation of the C3-OH resulted in simple competitive inhibitors of moderate potency, inversion of the C3 stereochemistry or substitution of fluorine for C3-OH resulted in slow-binding inhibitors of improved potency. The most potent inhibitor showed a K(I)(*) value of 0.43 microM.

摘要

S-核糖基高半胱氨酸酶（LuxS）催化S-核糖基高半胱氨酸（SRH）的硫醚键断裂，生成高半胱氨酸和4,5-二羟基-2,3-戊二酮（DPD），DPD是细菌细胞间通讯中2型自诱导物的前体。在本研究中，我们合成了几种在核糖C3位修饰的SRH类似物，作为LuxS的潜在抑制剂。虽然C3-OH的去除或甲基化产生了中等效力的简单竞争性抑制剂，但C3立体化学的反转或用氟取代C3-OH产生了效力提高的慢结合抑制剂。最有效的抑制剂的K(I)(*)值为0.43微摩尔。