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环状三萜类化合物的酶促合成

Enzymatic synthesis of cyclic triterpenes.

作者信息

Abe Ikuro

机构信息

School of Pharmaceutical Sciences, University of Shizuoka, and PRESTO, Japan Science and Technology Agency, 52-1 Yada, Shizuoka, 422-8526, Japan.

出版信息

Nat Prod Rep. 2007 Dec;24(6):1311-31. doi: 10.1039/b616857b. Epub 2007 Aug 7.

DOI:10.1039/b616857b
PMID:18033581
Abstract

This review covers recent advances in the chemistry and enzymology of squalene cyclase and oxidosqualene cyclase. The enzymatic cyclizations of squalene and oxidosqualene are the most remarkable steps in the biosynthesis of sterols and triterpenes. The polyenes are converted to various polycyclic triterpenes by different enzyme systems employing only small modification of the active-site. Recent crystallographic and structure-based mutagenesis studies as well as utilization of chemically synthesized active-site probes have begun to reveal intimate structural details of the enzyme-templated cyclization reactions. 126 References are cited.

摘要

本综述涵盖了角鲨烯环化酶和氧化角鲨烯环化酶在化学和酶学方面的最新进展。角鲨烯和氧化角鲨烯的酶促环化反应是甾醇和三萜生物合成中最显著的步骤。这些多烯通过不同的酶系统仅经活性位点的微小修饰就转化为各种多环三萜。最近的晶体学和基于结构的诱变研究以及化学合成活性位点探针的应用已开始揭示酶模板环化反应的详细结构细节。引用参考文献126篇。

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Enzymatic synthesis of cyclic triterpenes.环状三萜类化合物的酶促合成
Nat Prod Rep. 2007 Dec;24(6):1311-31. doi: 10.1039/b616857b. Epub 2007 Aug 7.
2
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Deletion of the Gly600 residue of Alicyclobacillus acidocaldarius squalene cyclase alters the substrate specificity into that of the eukaryotic-type cyclase specific to (3S)-2,3-oxidosqualene.嗜酸热脂环酸芽孢杆菌鲨烯环化酶的Gly600残基缺失会将底物特异性改变为对(3S)-2,3-氧化鲨烯具有特异性的真核型环化酶的底物特异性。
Angew Chem Int Ed Engl. 2004 Dec 10;43(48):6700-3. doi: 10.1002/anie.200461523.
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Squalene cyclase and oxidosqualene cyclase from a fern.来自一种蕨类植物的角鲨烯环化酶和氧化角鲨烯环化酶。
FEBS Lett. 2008 Jan 23;582(2):310-8. doi: 10.1016/j.febslet.2007.12.023. Epub 2007 Dec 26.
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Enzymatic cyclization of dioxidosqualene to heterocyclic triterpenes.二环氧角鲨烯酶促环化生成杂环三萜。
J Am Chem Soc. 2005 Dec 28;127(51):18008-9. doi: 10.1021/ja055822g.
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Profound insights into squalene cyclization.对角鲨烯环化的深刻见解。
Chem Biol. 2004 Jan;11(1):12-4. doi: 10.1016/j.chembiol.2004.01.008.
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Concerted nature of AB ring formation in the enzymatic cyclization of squalene to hopenes.角鲨烯酶促环化形成藿烯过程中AB环形成的协同性质。
Org Lett. 2004 May 27;6(11):1717-20. doi: 10.1021/ol0496125.
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An oxidosqualene cyclase makes numerous products by diverse mechanisms: a challenge to prevailing concepts of triterpene biosynthesis.氧化鲨烯环化酶通过多种机制产生众多产物:对三萜生物合成主流概念的挑战。
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9
Histidine residue at position 234 of oxidosqualene-lanosterol cyclase from saccharomyces cerevisiae simultaneously influences cyclization, rearrangement, and deprotonation reactions.来自酿酒酵母的氧化角鲨烯-羊毛甾醇环化酶第234位的组氨酸残基同时影响环化、重排和去质子化反应。
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Conversion of squalene to the pentacarbocyclic hopene.角鲨烯向五环藿烯的转化。
Chem Biol. 2004 Jan;11(1):121-6. doi: 10.1016/j.chembiol.2003.12.013.

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