Literature DB >> 24102367

Conformational preferences of zampanolide and dactylolide.

Erik M Larsen1, Matthew R Wilson, Jaroslav Zajicek, Richard E Taylor.   

Abstract

The solution conformation behavior of the macrolide core of microtubule-stabilizing agents (-)-zampanolide and (-)-dactylolide has been determined through a combination of high-field NMR experiments and computational modeling. Taken together, the results demonstrate that in solution both molecules exist as a mixture of three interconverting conformational families, one of which bears strong resemblance to zampanolide's tubulin-bound conformation.

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Year:  2013        PMID： 24102367      PMCID： PMC3946545          DOI： 10.1021/ol402462h

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


  19 in total

1.  Total synthesis of (+)-zampanolide.

Authors:  A B Smith; I G Safonov; R M Corbett
Journal:  J Am Chem Soc       Date:  2001-12-12       Impact factor: 15.419

2.  Zampanolide, a potent new microtubule-stabilizing agent, covalently reacts with the taxane luminal site in tubulin α,β-heterodimers and microtubules.

Authors:  Jessica J Field; Benet Pera; Enrique Calvo; Angeles Canales; Didier Zurwerra; Chiara Trigili; Javier Rodríguez-Salarichs; Ruth Matesanz; Arun Kanakkanthara; St John Wakefield; A Jonathan Singh; Jesús Jiménez-Barbero; Peter Northcote; John H Miller; Juan Antonio López; Ernest Hamel; Isabel Barasoain; Karl-Heinz Altmann; José Fernando Díaz
Journal:  Chem Biol       Date:  2012-06-22

3.  Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

Authors:  Matthew R Wilson; Richard E Taylor
Journal:  Org Lett       Date:  2012-06-21       Impact factor: 6.005

4.  The solution structure of (+)-spongistatin 1 in DMSO.

Authors:  Onur Atasoylu; George Furst; Christina Risatti; Amos B Smith
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

5.  Design, synthesis, and biological evaluation of diminutive forms of (+)-spongistatin 1: lessons learned.

Authors:  Amos B Smith; Christina A Risatti; Onur Atasoylu; Clay S Bennett; Junke Liu; Hongsheng Cheng; Karen TenDyke; Qunli Xu
Journal:  J Am Chem Soc       Date:  2011-08-12       Impact factor: 15.419

Review 6.  Microtubule-binding agents: a dynamic field of cancer therapeutics.

Authors:  Charles Dumontet; Mary Ann Jordan
Journal:  Nat Rev Drug Discov       Date:  2010-10       Impact factor: 84.694

7.  Rapid access to conformational analogues of (+)-peloruside A.

Authors:  Zhiming Zhao; Richard E Taylor
Journal:  Org Lett       Date:  2012-01-11       Impact factor: 6.005

8.  Studies toward the synthesis of (-)-zampanolide: preparation of N-acyl hemiaminal model systems.

Authors:  Dawn M Troast; John A Porco
Journal:  Org Lett       Date:  2002-03-21       Impact factor: 6.005

9.  Conformation-activity relationships in polyketide natural products: a new perspective on the rational design of epothilone analogues.

Authors:  Richard E Taylor; Yue Chen; Alicia Beatty; David C Myles; Yiqing Zhou
Journal:  J Am Chem Soc       Date:  2003-01-08       Impact factor: 15.419

10.  Total synthesis of (-)-zampanolide and structure-activity relationship studies on (-)-dactylolide derivatives.

Authors:  Didier Zurwerra; Florian Glaus; Leo Betschart; Julia Schuster; Jürg Gertsch; Walter Ganci; Karl-Heinz Altmann
Journal:  Chemistry       Date:  2012-11-07       Impact factor: 5.236
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  7 in total

Review 1.  Conformation-activity relationships of polyketide natural products.

Authors:  Erik M Larsen; Matthew R Wilson; Richard E Taylor
Journal:  Nat Prod Rep       Date:  2015-08       Impact factor: 13.423

2.  Unravelling the covalent binding of zampanolide and taccalonolide AJ to a minimalist representation of a human microtubule.

Authors:  Pedro A Sánchez-Murcia; Alberto Mills; Álvaro Cortés-Cabrera; Federico Gago
Journal:  J Comput Aided Mol Des       Date:  2019-05-31       Impact factor: 3.686

3.  Synthesis, conformational preferences, and biological activity of conformational analogues of the microtubule-stabilizing agents, (-)-zampanolide and (-)-dactylolide.

Authors:  Jeffrey L Henry; Matthew R Wilson; Michael P Mulligan; Taylor R Quinn; Dan L Sackett; Richard E Taylor
Journal:  Medchemcomm       Date:  2019-04-09       Impact factor: 3.597

4.  Insights into the Distinct Mechanisms of Action of Taxane and Non-Taxane Microtubule Stabilizers from Cryo-EM Structures.

Authors:  Elizabeth H Kellogg; Nisreen M A Hejab; Stuart Howes; Peter Northcote; John H Miller; J Fernando Díaz; Kenneth H Downing; Eva Nogales
Journal:  J Mol Biol       Date:  2017-01-17       Impact factor: 5.469

5.  Hydrocarbon Macrocycle Conformer Ensembles and 13 C-NMR Spectra.

Authors:  Fabian Bohle; Stefan Grimme
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-15       Impact factor: 16.823

6.  Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach.

Authors:  Jingjing Wang; Samuel Z Y Ting; Joanne E Harvey
Journal:  Beilstein J Org Chem       Date:  2015-10-05       Impact factor: 2.883

Review 7.  Zampanolide and dactylolide: cytotoxic tubulin-assembly agents and promising anticancer leads.

Authors:  Qiao-Hong Chen; David G I Kingston
Journal:  Nat Prod Rep       Date:  2014-09       Impact factor: 13.423
  7 in total

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