title: Alkyldihydropyrones, new polyketides synthesized by a type III polyketide synthase from Streptomyces reveromyceticus.
abstract: Genome sequencing allows a rapid and efficient identification of novel catalysts that produce novel secondary metabolites. Here we describe the catalytic properties of dihydropyrone synthase A (DpyA), a novel type III polyketide synthase encoded in a linear plasmid of Streptomyces reveromyceticus. Heterologous expression of dpyA led to the accumulation of alkyldihydropyrones A (1), B (2), C (3) and D (4), which are novel dihydropyran compounds that exhibit weak cytotoxicity against the leukemia cell line HL-60. DpyA catalyzes the condensation of β-hydroxyl acid thioester and methylmalonyl-CoA to yield a triketide intermediate that then undergoes lactonization of a secondary alcohol and a thioester to give alkyldihydropyrone.
authors.affiliation: Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka, Shizuoka, Japan.
authors.forename: Teruki
authors.initials: T
authors.lastname: Aizawa
authors.affiliation: Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka, Shizuoka, Japan.
authors.forename: Seung-Young
authors.initials: SY
authors.lastname: Kim
authors.affiliation: 1] Chemical Biology Research Group, RIKEN Center for Sustainable Resource Science, Saitama, Japan [2] Antibiotics Laboratory, RIKEN, Saitama, Japan.
authors.forename: Shunji
authors.initials: S
authors.lastname: Takahashi
authors.affiliation: Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka, Shizuoka, Japan.
authors.forename: Masahiko
authors.initials: M
authors.lastname: Koshita
authors.affiliation: Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka, Shizuoka, Japan.
authors.forename: Mioka
authors.initials: M
authors.lastname: Tani
authors.affiliation: Antibiotics Laboratory, RIKEN, Saitama, Japan.
authors.forename: Yushi
authors.initials: Y
authors.lastname: Futamura
authors.affiliation: 1] Chemical Biology Research Group, RIKEN Center for Sustainable Resource Science, Saitama, Japan [2] Antibiotics Laboratory, RIKEN, Saitama, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Osada
authors.affiliation: Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka, Shizuoka, Japan.
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Funa
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D018922:HL-60 Cells; D006801:Humans; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009904:Optical Rotation; D010957:Plasmids / Q000235:genetics; D048630:Polyketide Synthases / Q000235:genetics / Q000378:metabolism*; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013302:Streptomyces / Q000201:enzymology* / Q000235:genetics
chemical_list: D000970:Antineoplastic Agents; D061065:Polyketides; D011753:Pyrones; D048630:Polyketide Synthases