Literature DB >> 18062698

Computational studies of the tropone natural products, thiotropocin, tropodithietic acid, and troposulfenin. Significance of thiocarbonyl-enol tautomerism.

Edyta M Greer1, David Aebisher, Alexander Greer, Ronald Bentley.   

Abstract

Computations provide insight to the stability and isomeric possibilities of thiotropocin, tropodithietic acid, and troposulfenin. Thiotropocin and tropodithietic acid contain a flat 7-membered ring and delocalized pi-bonds similar to those of tropylium ion (C(7)H(7)(+)). Troposulfenin is far less stable; it contains a puckered tropone ring and localized bonds similar to 1,3,5-cycloheptatriene. A facile 1,5-hydrogen shift suggests that thiotropocin and tropodithietic acid exist as a pair of interconverting tautomers. Loss of an acidic proton from these three tautomers produces the same conjugate base structure.

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Year:  2007        PMID： 18062698     DOI： 10.1021/jo7018416

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  14 in total

1.  Influence of Iron on Production of the Antibacterial Compound Tropodithietic Acid and Its Noninhibitory Analog in Phaeobacter inhibens.

Authors:  Paul W D'Alvise; Christopher B W Phippen; Kristian F Nielsen; Lone Gram
Journal:  Appl Environ Microbiol       Date:  2015-10-30       Impact factor: 4.792

2.  MS-Derived Isotopic Fine Structure Reveals Forazoline A as a Thioketone-Containing Marine-Derived Natural Product.

Authors:  Fan Zhang; Thomas P Wyche; Yanlong Zhu; Doug R Braun; Jia-Xuan Yan; Shaurya Chanana; Ying Ge; Ilia A Guzei; Marc G Chevrette; Cameron R Currie; Michael G Thomas; Scott R Rajski; Tim S Bugni
Journal:  Org Lett       Date:  2020-02-04       Impact factor: 6.005

Review 3.  Quorum Sensing and Quorum Quenching in the Phycosphere of Phytoplankton: a Case of Chemical Interactions in Ecology.

Authors:  Jean Luc Rolland; Didier Stien; Sophie Sanchez-Ferandin; Raphaël Lami
Journal:  J Chem Ecol       Date:  2016-11-07       Impact factor: 2.626

4.  Synthesis of Naturally Occurring Tropones and Tropolones.

Authors:  Na Liu; Wangze Song; Casi M Schienebeck; Min Zhang; Weiping Tang
Journal:  Tetrahedron       Date:  2014-12-09       Impact factor: 2.457

5.  Resistance and tolerance to tropodithietic acid, an antimicrobial in aquaculture, is hard to select.

Authors:  Cisse Hedegaard Porsby; Mark A Webber; Kristian Fog Nielsen; Laura J V Piddock; Lone Gram
Journal:  Antimicrob Agents Chemother       Date:  2011-01-24       Impact factor: 5.191

6.  The Jekyll-and-Hyde chemistry of Phaeobacter gallaeciensis.

Authors:  Mohammad R Seyedsayamdost; Rebecca J Case; Roberto Kolter; Jon Clardy
Journal:  Nat Chem       Date:  2011-02-27       Impact factor: 24.427

7.  Mode of action and resistance studies unveil new roles for tropodithietic acid as an anticancer agent and the γ-glutamyl cycle as a proton sink.

Authors:  Maxwell Z Wilson; Rurun Wang; Zemer Gitai; Mohammad R Seyedsayamdost
Journal:  Proc Natl Acad Sci U S A       Date:  2016-01-22       Impact factor: 11.205

8.  Exo-metabolome of Pseudovibrio sp. FO-BEG1 analyzed by ultra-high resolution mass spectrometry and the effect of phosphate limitation.

Authors:  Stefano Romano; Thorsten Dittmar; Vladimir Bondarev; Ralf J M Weber; Mark R Viant; Heide N Schulz-Vogt
Journal:  PLoS One       Date:  2014-05-02       Impact factor: 3.240

9.  Characterisation of non-autoinducing tropodithietic Acid (TDA) production from marine sponge Pseudovibrio species.

Authors:  Catriona Harrington; F Jerry Reen; Marlies J Mooij; Fiona A Stewart; Jean-Baptiste Chabot; Antonio F Guerra; Frank O Glöckner; Kristian F Nielsen; Lone Gram; Alan D W Dobson; Claire Adams; Fergal O'Gara
Journal:  Mar Drugs       Date:  2014-12-10       Impact factor: 5.118

10.  Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid.

Authors:  Patrick Rabe; Tim A Klapschinski; Nelson L Brock; Christian A Citron; Paul D'Alvise; Lone Gram; Jeroen S Dickschat
Journal:  Beilstein J Org Chem       Date:  2014-08-06       Impact factor: 2.883
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