α-酮戊二酸/Fe(II)依赖性双加氧酶 VldW 负责 validamycin B 的形成。
The α-ketoglutarate/Fe(II)-dependent dioxygenase VldW is responsible for the formation of validamycin B.
机构信息
Department of Pharmaceutical Sciences, Oregon State University, 203 Pharmacy Building, Corvallis, OR 97331, USA.
出版信息
Chembiochem. 2012 Oct 15;13(15):2209-11. doi: 10.1002/cbic.201200464. Epub 2012 Sep 7.
Abstract
From A to B: Through detailed biochemical investigations, we discovered that VldW, an α-ketoglutarate/Fe(II)-dependent dioxygenase, regioselectively hydroxylates validamycin A to validamycin B. The results provide insights into the biosynthesis of hydroxylated validamycins and could be used to control the metabolic outcomes of the validamycin pathway.
摘要
从 A 到 B：通过详细的生化研究，我们发现 VldW 是一种 α-酮戊二酸/Fe(II)依赖性双加氧酶，能区域选择性地将 validamycin A 羟基化为 validamycin B。研究结果为羟基化 validamycins 的生物合成提供了新见解，并可用于控制 validamycin 途径的代谢产物。
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2
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3
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Nat Chem Biol. 2010 Apr;6(4):273-5. doi: 10.1038/nchembio.317. Epub 2010 Mar 14.
4
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Nat Prod Rep. 2007 Apr;24(2):358-92. doi: 10.1039/b603816f. Epub 2006 Dec 21.
5
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6
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Anal Biochem. 2006 Jun 1;353(1):69-74. doi: 10.1016/j.ab.2006.03.033. Epub 2006 Apr 19.
7
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