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Solanapyrone Synthase, a Possible Diels–Alderase and Iterative Type I Polyketide Synthase Encoded in a Biosynthetic Gene Cluster from Alternaria solani
Author(s) -
Kasahara Ken,
Miyamoto Takanori,
Fujimoto Takashi,
Oguri Hiroki,
Tokiwano Tetsuo,
Oikawa Hideaki,
Ebizuka Yutaka,
Fujii Isao
Publication year - 2010
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.201000173
Subject(s) - polyketide synthase , alternaria solani , atp synthase , biochemistry , gene cluster , biology , aspergillus oryzae , biosynthesis , enzyme , polyketide , gene , chemistry , blight , horticulture
The solanapyrone biosynthetic gene cluster was cloned from Alternaria solani . It consists of six genes— sol1–6 —coding for a polyketide synthase, an O ‐methyltransferase, a dehydrogenase, a transcription factor, a flavin‐dependent oxidase, and cytochrome P450. The prosolanapyrone synthase (PSS) encoded by sol1 was expressed in Aspergillus oryzae and its product was identified as desmethylprosolanapyrone I ( 8 ). Although PSS is closely related to the PKSs/Diels–Alderases LovB and MlcA of lovastatin and compactin biosynthesis, it did not catalyze cycloaddition. Sol5, encoding a flavin‐dependent oxidase (solanapyrone synthase, SPS), was expressed in Pichia pastoris and purified. The purified recombinant SPS showed activity for the formation of (−)‐solanapyrone A ( 1 ) from achiral prosolanapyrone II ( 2 ), establishing that this single enzyme catalyzes both the oxidation and the subsequent cycloaddition reaction, possibly as a Diels–Alder enzyme.