Literature DB >> 17107082

Verticilide: elucidation of absolute configuration and total synthesis.

Souichi Monma1, Toshiaki Sunazuka, Kenichiro Nagai, Takahiro Arai, Kazuro Shiomi, Ryosuke Matsui, Satoshi Omura.   

Abstract

Verticilide (1) is a 24-membered cyclic depsipeptide isolated from the culture broth of Verticillium sp. FKI-1033. It inhibits ryanodine binding to ryanodine receptor (RyR) and has insecticidal activity. The stereochemistry of 2-hydroxyheptanoic acid in verticilide was elucidated by chiral HPLC analysis of the degradation product 6 and synthetic (+) and (-)-6. We also describe the practical total synthesis of verticilide. [reaction: see text].

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Year:  2006        PMID: 17107082     DOI: 10.1021/ol0623365

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control.

Authors:  Suzanne M Batiste; Jeffrey N Johnston
Journal:  Proc Natl Acad Sci U S A       Date:  2016-12-14       Impact factor: 11.205

2.  Ring Size as an Independent Variable in Cyclooligomeric Depsipeptide Antiarrhythmic Activity.

Authors:  Abigail N Smith; Daniel J Blackwell; Bjorn C Knollmann; Jeffrey N Johnston
Journal:  ACS Med Chem Lett       Date:  2021-11-23       Impact factor: 4.345

3.  Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.

Authors:  Hai-Jun Zhang; Alexander W Schuppe; Shi-Tao Pan; Jin-Xiang Chen; Bo-Ran Wang; Timothy R Newhouse; Liang Yin
Journal:  J Am Chem Soc       Date:  2018-04-09       Impact factor: 15.419

4.  Aspergillus niger is a superior expression host for the production of bioactive fungal cyclodepsipeptides.

Authors:  Simon Boecker; Stefan Grätz; Dennis Kerwat; Lutz Adam; David Schirmer; Lennart Richter; Tabea Schütze; Daniel Petras; Roderich D Süssmuth; Vera Meyer
Journal:  Fungal Biol Biotechnol       Date:  2018-03-02

5.  Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides.

Authors:  Assunta D'Amato; Giorgio Della Sala; Irene Izzo; Chiara Costabile; Yuichi Masuda; Francesco De Riccardis
Journal:  Molecules       Date:  2018-07-19       Impact factor: 4.411

6.  The Formation of Impossible Rings in Macrocyclooligomerizations for Cyclodepsipeptide Synthesis: The 18-from-12 Paradox.

Authors:  Abigail N Smith; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2021-06-07       Impact factor: 4.354

Review 7.  Risks of Mycotoxins from Mycoinsecticides to Humans.

Authors:  Qiongbo Hu; Fuxia Li; Yuping Zhang
Journal:  Biomed Res Int       Date:  2016-04-10       Impact factor: 3.411

8.  Anthelmintic PF1022A: stepwise solid-phase synthesis of a cyclodepsipeptide containing N-methyl amino acids.

Authors:  Sebastian Lüttenberg; Frank Sondermann; Jürgen Scherkenbeck
Journal:  Tetrahedron       Date:  2011-12-16       Impact factor: 2.457

  8 in total

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