真菌芳香聚酮化合物形成的新见解。
New insights into the formation of fungal aromatic polyketides.
机构信息
Department of Biological Chemistry & Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue, Boston, Massachusetts 02115, USA.
出版信息
Nat Rev Microbiol. 2010 Dec;8(12):879-89. doi: 10.1038/nrmicro2465.
Abstract
Fungal aromatic polyketides constitute a large family of bioactive natural products and are synthesized by the non-reducing group of iterative polyketide synthases (PKSs). Their diverse structures arise from selective enzymatic modifications of reactive, enzyme-bound poly-β-keto intermediates. How iterative PKSs control starter unit selection, polyketide chain initiation and elongation, intermediate folding and cyclization, selective redox or modification reactions during assembly, and product release are central mechanistic questions underlying iterative catalysis. This Review highlights recent insights into these questions, with a particular focus on the biosynthetic programming of fungal aromatic polyketides, and draws comparisons with the allied biosynthetic processes in bacteria.
摘要
真菌芳香聚酮化合物构成了一大类具有生物活性的天然产物，由非还原性的多酮合酶（PKSs）组合成。它们的多种结构来源于对反应性、酶结合的多β-酮中间产物的选择性酶促修饰。迭代 PKS 如何控制起始单元选择、聚酮链起始和延伸、中间折叠和环化、组装过程中的选择性氧化还原或修饰反应以及产物释放，这些都是迭代催化的核心机制问题。这篇综述强调了最近对这些问题的深入了解，特别关注真菌芳香聚酮的生物合成编程，并与细菌中相关的生物合成过程进行了比较。
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本文引用的文献
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Chem Biol. 2010 May 28;17(5):483-94. doi: 10.1016/j.chembiol.2010.03.015.
2
Classification, prediction, and verification of the regioselectivity of fungal polyketide synthase product template domains.真菌聚酮合酶产物模板域的区域选择性的分类、预测和验证。
J Biol Chem. 2010 Jul 23;285(30):22764-73. doi: 10.1074/jbc.M110.128504. Epub 2010 May 17.
3
Cyclization of aromatic polyketides from bacteria and fungi.细菌和真菌中芳香族聚酮化合物的环化作用。
Nat Prod Rep. 2010 Jun;27(6):839-68. doi: 10.1039/b911518h. Epub 2010 Mar 31.
4
HypC, the anthrone oxidase involved in aflatoxin biosynthesis.HypC，参与黄曲霉毒素生物合成的蒽酮氧化酶。
Appl Environ Microbiol. 2010 May;76(10):3374-7. doi: 10.1128/AEM.02495-09. Epub 2010 Mar 26.
5
Structure and function of an iterative polyketide synthase thioesterase domain catalyzing Claisen cyclization in aflatoxin biosynthesis.结构与功能的迭代聚酮合酶硫酯酶域催化克莱森环化在黄曲霉毒素生物合成。
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6
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