利用具有宽松底物特异性的链霉菌异戊烯基转移酶进行异戊烯基化芳香小分子的化学酶法合成。
Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities.
作者信息
Kumano Takuto, Richard Stéphane B, Noel Joseph P, Nishiyama Makoto, Kuzuyama Tomohisa
机构信息
Biotechnology Research Center, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan.
出版信息
Bioorg Med Chem. 2008 Sep 1;16(17):8117-26. doi: 10.1016/j.bmc.2008.07.052. Epub 2008 Jul 24.
NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3(2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism.
NphB是一种来自链霉菌属CL190菌株的可溶性异戊二烯基转移酶，在抗氧化剂萘萜素的生物合成过程中，它将一个香叶基连接到一个由1,3,6,8 - 四羟基萘衍生的聚酮化合物上。在此，我们报道了使用两种异戊二烯基转移酶NphB和来自天蓝色链霉菌A3(2)的NphB同源物SCO7190作为生物催化剂，从包括黄酮类化合物在内的芳香族底物出发，进行多种烯丙基化化合物的多酶催化合成。NphB催化多种含羟基芳香族受体的基于碳 - 碳和基于碳 - 氧的香叶基化反应。因此，这种使用异戊二烯基转移酶的简单方法可用于探索具有生物活性的新型烯丙基化芳香族化合物。对NphB的动力学研究表明，烯丙基化反应遵循有序的顺序机制。
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