Literature DB >> 19572566

New sources of chemical diversity inspired by biosynthesis: rational design of a potent epothilone analogue.

Jeffrey D Frein1, Richard E Taylor, Dan L Sackett.   

Abstract

A concise total synthesis of (S)-14-methoxyepothilone D has been accomplished. (S)-14-Methoxyepothilone D represents a conceptually novel example of polyketide analogue design based on an alternative biogenetic pattern of extender units. The significant biological activity observed for this compound provides a foundation to support studies designed to prepare derivatives of this type through fermentation of genetically engineered organisms expressing the epothilone PKS gene cluster.

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Year:  2009        PMID： 19572566      PMCID： PMC2736359          DOI： 10.1021/ol900971r

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


  12 in total

1.  The high-resolution solution structure of epothilone A bound to tubulin: an understanding of the structure-activity relationships for a powerful class of antitumor agents.

Authors:  Teresa Carlomagno; Marcel J J Blommers; Jens Meiler; Wolfgang Jahnke; Thomas Schupp; Frank Petersen; Dieter Schinzer; Karl-Heinz Altmann; Christian Griesinger
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-06       Impact factor: 15.336

2.  Total synthesis of epothilones B and D.

Authors:  R E Taylor; Y Chen
Journal:  Org Lett       Date:  2001-07-12       Impact factor: 6.005

3.  Much anticipated--the bioactive conformation of epothilone and its binding to tubulin.

Authors:  Dirk W Heinz; Wolf-Dieter Schubert; Gerhard Höfle
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-18       Impact factor: 15.336

4.  Evolution of polyketide synthases in bacteria.

Authors:  Christian P Ridley; Ho Young Lee; Chaitan Khosla
Journal:  Proc Natl Acad Sci U S A       Date:  2008-02-04       Impact factor: 11.205

5.  Cloning and heterologous expression of the epothilone gene cluster.

Authors:  L Tang; S Shah; L Chung; J Carney; L Katz; C Khosla; B Julien
Journal:  Science       Date:  2000-01-28       Impact factor: 47.728

6.  Hydroxymalonyl-acyl carrier protein (ACP) and aminomalonyl-ACP are two additional type I polyketide synthase extender units.

Authors:  Yolande A Chan; Michael T Boyne; Angela M Podevels; Amy K Klimowicz; Jo Handelsman; Neil L Kelleher; Michael G Thomas
Journal:  Proc Natl Acad Sci U S A       Date:  2006-09-18       Impact factor: 11.205

7.  Diastereoselective titanium enolate aldol reaction for the total synthesis of epothilones.

Authors:  Guido Koch; Olivier Loiseleur; Daniel Fuentes; Andrea Jantsch; Karl-Heinz Altmann
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

8.  Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis.

Authors:  K Takai; M Tagashira; T Kuroda; K Oshima; K Utimoto; H Nozaki
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

9.  Conformation-activity relationships in polyketide natural products. Towards the biologically active conformation of epothilone.

Authors:  Richard E Taylor; Yue Chen; Gabriel M Galvin; Praveen K Pabba
Journal:  Org Biomol Chem       Date:  2003-11-20       Impact factor: 3.876

10.  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
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  4 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.  Thermodynamic control of 1,3-boratropic shifts of α- and γ-stannyl-substituted allylboranes: hyperconjugation outweighs steric effects.

Authors:  Preston S Stewart; Ming Chen; William R Roush; Daniel H Ess
Journal:  Org Lett       Date:  2011-02-16       Impact factor: 6.005

3.  Enantioselective synthesis of (E)-delta-stannyl homoallylic alcohols via aldehyde allylboration using alpha-stannylallylboranes generated by allene hydroboration followed by a highly diastereoselective 1,3-boratropic shift.

Authors:  Ming Chen; Daniel H Ess; William R Roush
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

4.  Synthesis and Biological Evaluation of 7-Deoxy-Epothilone Analogues.

Authors:  Laura M Woods; Joseph W Arico; Jeffrey D Frein; Dan L Sackett; Richard E Taylor
Journal:  Int J Mol Sci       Date:  2017-03-17       Impact factor: 5.923
  4 in total

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