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Characterization of the Biosynthesis Gene Cluster for Alkyl‐ O ‐Dihydrogeranyl‐Methoxyhydroquinones in Actinoplanes missouriensis
Author(s) -
Awakawa Takayoshi,
Fujita Nobuyuki,
Hayakawa Masayuki,
Ohnishi Yasuo,
Horinouchi Sueharu
Publication year - 2011
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201000628
Subject(s) - gene cluster , prenyltransferase , biosynthesis , heterologous expression , stereochemistry , alkyl , biochemistry , polyketide , biology , prenylation , gene , polyketide synthase , chemistry , enzyme , organic chemistry , recombinant dna
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 C 16–17 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 C 16–17 fatty acids. In contrast, A. missouriensis was found to produce 6‐alkyl‐4‐ O ‐dihydrogeranyl‐2‐methoxyhydroquinones derived from C 16–18 fatty acids by the function of the agq gene cluster. All of these prenylated phenolic lipids were novel compounds.