Your browser doesn't support javascript.
loading
Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide.
Seo, Mitsuki; Du, Danyao; Katsuyama, Yohei; Katsuta, Ryo; Yajima, Arata; Nukada, Tomoo; Ohnishi, Yasuo; Ishigami, Ken.
Afiliação
  • Seo M; Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan.
  • Du D; Department of Biotechnology, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan.
  • Katsuyama Y; Department of Biotechnology, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan.
  • Katsuta R; Collaborative Research Institute for Innovative Microbiology, The University of Tokyo, Bunkyo-ku, Tokyo, Japan.
  • Yajima A; Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan.
  • Nukada T; Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan.
  • Ohnishi Y; Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan.
  • Ishigami K; Department of Biotechnology, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan.
Biosci Biotechnol Biochem ; 85(1): 148-153, 2021 Jan 07.
Article em En | MEDLINE | ID: mdl-33577653
ABSTRACT
Ishigamide was isolated as a metabolite of a recombinant strain of Streptomyces sp. MSC090213JE08 and its unsaturated fatty acid moiety has been confirmed in vitro to be synthesized by a type II PKS. Biosynthesis of such a highly reduced polyketide by a type II PKS is worthy of note. However, absolute configuration of ishigamide remained unknown. (R)-Ishigamide was synthesized enantioselectively employing Stille coupling and Wittig reaction between three units, vinyl iodide, stannyldienal, and Wittig salt. Stereochemistry of natural ishigamide was determined to be R by chiral HPLC analysis comparing with the synthesized standard.
Assuntos
Palavras-chave
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Policetídeos Idioma: En Ano de publicação: 2021 Tipo de documento: Article
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Policetídeos Idioma: En Ano de publicação: 2021 Tipo de documento: Article