Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide | Zendy

Mitsuki Seo | Zendy; Danyao Du | Zendy; Yohei Katsuyama | Zendy; Ryo Katsuta | Zendy; Arata Yajima | Zendy; Tomoo Nukada | Zendy; Yasuo Ohnishi | Zendy; Ken Ishigami | Zendy

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Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide

Author(s) -

Mitsuki Seo,

Danyao Du,

Yohei Katsuyama,

Ryo Katsuta,

Arata Yajima,

Tomoo Nukada,

Yasuo Ohnishi,

Ken Ishigami

Publication year - 2021

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1093/bbb/zbaa023

Subject(s) - polyketide , enantioselective synthesis , moiety , wittig reaction , stille reaction , stereochemistry , metabolite , chemistry , absolute configuration , iodide , biosynthesis , organic chemistry , catalysis , biochemistry , enzyme

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.

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