Literature DB >> 22114734

Synthesis enables a structural revision of the Mycobacterium tuberculosis-produced diterpene, edaxadiene.

Jillian E Spangler1, Cheryl A Carson, Erik J Sorensen.   

Abstract

A stereodivergent synthesis of the [3.3.1] bicyclic core of edaxadiene was completed utilizing a key intramolecular oxidative ketone allylation. Significant discrepancies between the spectroscopic data obtained for the synthetic construct and the natural isolate raised questions about the structural assignment of edaxadiene. A subsequent structural reassignment was validated by completion of a total synthesis of the correct structure of the natural product.

Entities:  

Year:  2010        PMID： 22114734      PMCID： PMC3221386          DOI： 10.1039/C0SC00284D

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  10 in total

1.  Mn(III)-Based Oxidative Free-Radical Cyclizations of Unsaturated Ketones.

Authors:  Bridget McCarthy Cole; Luning Han; Barry B. Snider
Journal:  J Org Chem       Date:  1996-11-01       Impact factor: 4.354

2.  Mycobacterium tuberculosis H37Rv3377c encodes the diterpene cyclase for producing the halimane skeleton.

Authors:  Chiaki Nakano; Tomoo Okamura; Tsutomu Sato; Tohru Dairi; Tsutomu Hoshino
Journal:  Chem Commun (Camb)       Date:  2005-01-04       Impact factor: 6.222

3.  Racemic and asymmetric Diels-Alder reactions of 1-(2-oxazolidinon-3-yl)-3-siloxy-1,3-butadienes.

Authors:  J M Janey; T Iwama; S A Kozmin; V H Rawal
Journal:  J Org Chem       Date:  2000-12-29       Impact factor: 4.354

4.  Synthesis of (+/-)-nosyberkol (isotuberculosinol, revised structure of edaxadiene) and (+/-)-tuberculosinol.

Authors:  Nathan Maugel; Francis M Mann; Matthew L Hillwig; Reuben J Peters; Barry B Snider
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

5.  Asmarines I, J, and K and nosyberkol: four new compounds from the marine sponge Raspailia sp.

Authors:  Amira Rudi; Maurice Aknin; Emile Gaydou; Yoel Kashman
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

Review 6.  Who puts the tubercle in tuberculosis?

Authors:  David G Russell
Journal:  Nat Rev Microbiol       Date:  2006-12-11       Impact factor: 60.633

7.  Isolation of Mycobacterium tuberculosis mutants defective in the arrest of phagosome maturation.

Authors:  Kevin Pethe; Dana L Swenson; Sylvie Alonso; Jennifer Anderson; Carren Wang; David G Russell
Journal:  Proc Natl Acad Sci U S A       Date:  2004-08-31       Impact factor: 11.205

8.  A rapid, asymmetric synthesis of the decahydrofluorene core of the hirsutellones.

Authors:  S David Tilley; Keith P Reber; Erik J Sorensen
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

9.  Edaxadiene: a new bioactive diterpene from Mycobacterium tuberculosis.

Authors:  Francis M Mann; Meimei Xu; Xiaoming Chen; D Bruce Fulton; David G Russell; Reuben J Peters
Journal:  J Am Chem Soc       Date:  2009-12-09       Impact factor: 15.419

10.  Characterization and inhibition of a class II diterpene cyclase from Mycobacterium tuberculosis: implications for tuberculosis.

Authors:  Francis M Mann; Sladjana Prisic; Huayou Hu; Meimei Xu; Robert M Coates; Reuben J Peters
Journal:  J Biol Chem       Date:  2009-07-02       Impact factor: 5.157
  10 in total
  9 in total

1.  Stereoselective Synthesis of 1-Tuberculosinyl Adenosine; a Virulence Factor of Mycobacterium tuberculosis.

Authors:  Jeffrey Buter; Dorus Heijnen; Ieng Chim Wan; F Matthias Bickelhaupt; David C Young; Edwin Otten; D Branch Moody; Adriaan J Minnaard
Journal:  J Org Chem       Date:  2016-07-26       Impact factor: 4.354

2.  Magnesium depletion triggers production of an immune modulating diterpenoid in Mycobacterium tuberculosis.

Authors:  Francis M Mann; Brian C VanderVen; Reuben J Peters
Journal:  Mol Microbiol       Date:  2011-01-25       Impact factor: 3.501

3.  Genetics of Capsular Polysaccharides and Cell Envelope (Glyco)lipids.

Authors:  Mamadou Daffé; Dean C Crick; Mary Jackson
Journal:  Microbiol Spectr       Date:  2014

4.  Isotuberculosinol: the unusual case of an immunomodulatory diterpenoid from Mycobacterium tuberculosis.

Authors:  Francis M Mann; Reuben J Peters
Journal:  Medchemcomm       Date:  2012-08-01       Impact factor: 3.597

5.  Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

Authors:  Junjia Liu; T Aaron Bedell; Julian G West; Erik J Sorensen
Journal:  Tetrahedron       Date:  2016-01-28       Impact factor: 2.457

Review 6.  Chemical Synthesis of Cell Wall Constituents of Mycobacterium tuberculosis.

Authors:  Mira Holzheimer; Jeffrey Buter; Adriaan J Minnaard
Journal:  Chem Rev       Date:  2021-06-30       Impact factor: 60.622

Review 7.  Antibacterial Natural Halimanes: Potential Source of Novel Antibiofilm Agents.

Authors:  Ignacio E Tobal; Alejandro M Roncero; Rosalina F Moro; David Díez; Isidro S Marcos
Journal:  Molecules       Date:  2020-04-08       Impact factor: 4.411

8.  Functional characterization and evolution of the isotuberculosinol operon in Mycobacterium tuberculosis and related Mycobacteria.

Authors:  Francis M Mann; Meimei Xu; Emily K Davenport; Reuben J Peters
Journal:  Front Microbiol       Date:  2012-10-12       Impact factor: 5.640

9.  Structure and inhibition of tuberculosinol synthase and decaprenyl diphosphate synthase from Mycobacterium tuberculosis.

Authors:  Hsiu-Chien Chan; Xinxin Feng; Tzu-Ping Ko; Chun-Hsiang Huang; Yumei Hu; Yingying Zheng; Shannon Bogue; Chiaki Nakano; Tsutomu Hoshino; Lilan Zhang; Pin Lv; Wenting Liu; Dean C Crick; Po-Huang Liang; Andrew H-J Wang; Eric Oldfield; Rey-Ting Guo
Journal:  J Am Chem Soc       Date:  2014-02-05       Impact factor: 15.419
  9 in total

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