Literature DB >> 17020294

Stereochemical determination of Archazolid A and B, highly potent vacuolar-type ATPase inhibitors from the Myxobacterium Archangium gephyra.

Jorma Hassfeld1, Christophe Farès, Heinrich Steinmetz, Teresa Carlomagno, Dirk Menche.   

Abstract

[structure: see text] The relative and absolute stereochemistry of the structurally unique 24-membered myxobacterial macrolides archazolid A and B, highly potent vacuolar-type ATPase (V-ATPase) inhibitors in vitro and in vivo, was determined on the basis of a combination of extensive high-field NMR studies, including J-based configuration analysis, molecular modeling, and chemical methods.

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Year:  2006        PMID: 17020294     DOI: 10.1021/ol061831y

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


  5 in total

1.  Archazolid A binds to the equatorial region of the c-ring of the vacuolar H+-ATPase.

Authors:  Svenja Bockelmann; Dirk Menche; Sven Rudolph; Tobias Bender; Stephanie Grond; Paultheo von Zezschwitz; Stephen P Muench; Helmut Wieczorek; Markus Huss
Journal:  J Biol Chem       Date:  2010-09-30       Impact factor: 5.157

2.  Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling.

Authors:  Zhihong Huang; Ei-ichi Negishi
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

3.  Machine learning estimates of natural product conformational energies.

Authors:  Matthias Rupp; Matthias R Bauer; Rainer Wilcken; Andreas Lange; Michael Reutlinger; Frank M Boeckler; Gisbert Schneider
Journal:  PLoS Comput Biol       Date:  2014-01-16       Impact factor: 4.475

Review 4.  Total syntheses of the archazolids: an emerging class of novel anticancer drugs.

Authors:  Stephan Scheeff; Dirk Menche
Journal:  Beilstein J Org Chem       Date:  2017-06-07       Impact factor: 2.883

Review 5.  Design and Synthesis of Simplified Polyketide Analogs: New Modalities beyond the Rule of 5.

Authors:  Dirk Menche
Journal:  ChemMedChem       Date:  2021-05-05       Impact factor: 3.466

  5 in total

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