Characterization of the Biosynthesis Gene Cluster for Alkyl-O-Dihydrogeranyl-Methoxyhydroquinones in Actinoplanes missouriensis
Characterization of the Biosynthesis Gene Cluster for Alkyl-O-Dihydrogeranyl-Methoxyhydroquinones in Actinoplanes missouriensis
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DOI：
10.1002/cbic.201000628
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发表时间：
2011-02-11
期刊：
影响因子：
3.2
通讯作者：
Horinouchi, Sueharu
中科院分区：
文献类型：
--
作者：
Awakawa, Takayoshi;Fujita, Nobuyuki;Horinouchi, Sueharu
在密苏里游动放线菌基因组中发现了一个聚酮生物合成基因簇（agq）。变铅青链霉菌表达编码III型聚酮合酶的agqA，主要从C16-17脂肪酸产生烷基间苯二酚。agq基因在S.变青聚糖表明同源聚酮修饰酶的功能;单加氧酶AgqB使烷基间苯二酚羟基化以产生6-烷基-2-羟基对苯二酚，甲基转移酶AgqC催化烷基-羟基对苯二酚的O-甲基化以产生6-烷基-2-甲氧基对苯二酚，和UbiA样异戊二烯基转移酶AgqD将异戊二烯基连接到烷基-甲氧基氢醌的C-4羟基上，产生6-烷基-4-O-香叶基-2-甲基-异戊烯基。衍生自C16-17脂肪酸的6-烷基-4-O-二氢法呢基-2-甲氧基氢醌。与此相反，A.发现missouriensis通过agq基因簇的功能产生衍生自C16-18脂肪酸的6-烷基-4-O-二氢香叶基-2-甲氧基氢醌。所有这些异戊二烯化的酚脂是新的化合物。
A polyketide biosynthesis gene cluster (agq) was found on the genome of a rare actinomycete, Actinoplanes missouriensis. Streptomyces lividans expressing agqA encoding a type III polyketide synthase produced alkylresorcinols mainly from C16-17 fatty acids. Heterologous expression of the agq genes in S. lividans indicated the function of cognate polyketide modification enzymes; a monooxygenase AgqB hydroxylates the alkylresorcinols to yield 6-alkyl-2-hydroxyhydroquinones, a methyltransferase AgqC catalyzes O-methylation of the alkyl-hydroxyhydroquinones to yield 6-alkyl-2-methoxyhydroquinones, and a UbiA-like prenyltransferase AgqD attaches a prenyl group to the C-4 hydroxy group of the alkyl-methoxyhydroquinones to yield 6-alkyl-4-O-geranyl-2-methoxyhydroquinones and 6-alkyl-4-O-dihydrofarnesyl-2-methoxyhydroquinones derived from C16-17 fatty acids. In contrast, A. missouriensis was found to produce 6-alkyl-4-O-dihydrogeranyl-2-methoxyhydroquinones derived from C16-18 fatty acids by the function of the agq gene cluster. All of these prenylated phenolic lipids were novel compounds.