Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide. Issue 1 (7th January 2021)

• Record Type: Journal Article
• Authors: Seo, Mitsuki; Du, Danyao; Katsuyama, Yohei; Katsuta, Ryo; Yajima, Arata; Nukada, Tomoo; Ohnishi, Yasuo; Ishigami, Ken
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 85:Issue 1(2021)
• Page Start: 148
• Page End: 153
• Publication Date: 2021-01-07
• Subjects: ishigamide -- determination of absolute configuration -- tetraene; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1093/bbb/zbaa023
• Languages: English
• ISSNs: 0916-8451

Abstract

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. Graphical Abstract: