Literature DB >> 21989459

Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis.

Miho Uchida1, Satoshi Takamatsu, Shiho Arima, Kiyoko T Miyamoto, Shigeru Kitani, Takuya Nihira, Haruo Ikeda, Tohru Nagamitsu.   

Abstract

The first total synthesis of extracellular factor, "Avenolide", in Streptomyces avermitilis has been achieved using a convergent approach. The stereogenic centers in two key segments were installed using Sharpless epoxidation and dihydroxylation. This synthetic study allowed the determination of the absolute configuration of avenolide as 4S,10R, and yielded important information on its structure-activity relationship.

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21989459     DOI: 10.1038/ja.2011.90

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  7 in total

1.  Avenolide, a Streptomyces hormone controlling antibiotic production in Streptomyces avermitilis.

Authors:  Shigeru Kitani; Kiyoko T Miyamoto; Satoshi Takamatsu; Elisa Herawati; Hiroyuki Iguchi; Kouhei Nishitomi; Miho Uchida; Tohru Nagamitsu; Satoshi Omura; Haruo Ikeda; Takuya Nihira
Journal:  Proc Natl Acad Sci U S A       Date:  2011-09-19       Impact factor: 11.205

Review 2.  Genome mining of the Streptomyces avermitilis genome and development of genome-minimized hosts for heterologous expression of biosynthetic gene clusters.

Authors:  Haruo Ikeda; Shin-ya Kazuo; Satoshi Omura
Journal:  J Ind Microbiol Biotechnol       Date:  2013-08-29       Impact factor: 3.346

3.  Discovering potential Streptomyces hormone producers by using disruptants of essential biosynthetic genes as indicator strains.

Authors:  Nguyen B Thao; Shigeru Kitani; Hiroko Nitta; Toshiya Tomioka; Takuya Nihira
Journal:  J Antibiot (Tokyo)       Date:  2017-07-19       Impact factor: 2.649

Review 4.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

5.  Visualization of cortex organization and dynamics in microorganisms, using total internal reflection fluorescence microscopy.

Authors:  Felix Spira; Julia Dominguez-Escobar; Nikola Müller; Roland Wedlich-Söldner
Journal:  J Vis Exp       Date:  2012-05-01       Impact factor: 1.355

6.  Chiral Bifunctional Phosphine Ligand-Enabled Cooperative Cu Catalysis: Formation of Chiral α,β-Butenolides via Highly Enantioselective γ-Protonation.

Authors:  Xinpeng Cheng; Tianyou Li; Kaylaa Gutman; Liming Zhang
Journal:  J Am Chem Soc       Date:  2021-07-15       Impact factor: 16.383

7.  Biochemical basis for the regulation of biosynthesis of antiparasitics by bacterial hormones.

Authors:  Iti Kapoor; Philip Olivares; Satish K Nair
Journal:  Elife       Date:  2020-06-08       Impact factor: 8.140

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.