Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide-Reference-Cited by-同舟云学术

Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide

Published:2021-01 Issue:1 Volume:85 Page:148-153
ISSN:1347-6947
Container-title:Bioscience, Biotechnology, and Biochemistry
language:en
Short-container-title:

Author:

Seo Mitsuki¹,Du Danyao²,Katsuyama Yohei²³,Katsuta Ryo¹^ORCID,Yajima Arata¹^ORCID,Nukada Tomoo¹,Ohnishi Yasuo²³,Ishigami Ken¹^ORCID

Affiliation:

1. Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan

2. Department of Biotechnology, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan

3. Collaborative Research Institute for Innovative Microbiology, The University of Tokyo, Bunkyo-ku, Tokyo, Japan

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.

Publisher

Oxford University Press (OUP)

Subject

Organic Chemistry,Molecular Biology,Applied Microbiology and Biotechnology,General Medicine,Biochemistry,Analytical Chemistry,Biotechnology

Link

http://academic.oup.com/bbb/article-pdf/85/1/148/36669173/zbaa023.pdf

Reference23 articles.

1. Asymmetric Pauson-Khand cyclization; a formal total synthesis of natural brefeldin A;Bernardas;J Org Chem,1995

2. New simocyclinones: Surprising evolutionary and biosynthetic insights;Bilyk;ACS Chem Biol,2016

3. Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities;Dermenci;Chem Sci,2011

4. Structural basis for selectivity in a highly reducing type II polyketide synthase;Du;Nat Chem Biol,2020

5. Production of a novel amide-containing polyene by activating a cryptic biosynthetic gene cluster in Streptomyces sp. MSC090213JE08;Du;ChemBioChem,2016

Cited by 1 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Biocontrol potential of volatile organic compounds produced by Streptomyces corchorusii CG-G2 to strawberry anthracnose caused by Colletotrichum gloeosporioides;Food Chemistry;2024-03