Characterization of the biosynthesis gene cluster for alkyl-O-dihydrogeranyl-methoxyhydroquinones in Actinoplanes missouriensis.
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.
Department of Biotechnology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
Takayoshi
T
Awakawa
Nobuyuki
N
Fujita
Masayuki
M
Hayakawa
Yasuo
Y
Ohnishi
Sueharu
S
Horinouchi
D004122:Dimethylallyltranstransferase / Q000235:genetics / Q000378:metabolism; D005227:Fatty Acids / Q000737:chemistry; D006873:Hydroquinones / Q000737:chemistry / Q000378:metabolism*; D008848:Micromonosporaceae / Q000201:enzymology* / Q000235:genetics; D009097:Multienzyme Complexes / Q000235:genetics* / Q000378:metabolism; D005810:Multigene Family; D048630:Polyketide Synthases / Q000235:genetics / Q000378:metabolism
D005227:Fatty Acids; D006873:Hydroquinones; D009097:Multienzyme Complexes; D048630:Polyketide Synthases; D004122:Dimethylallyltranstransferase; C031927:hydroquinone