Literature DB >> 12583750

Toward a structure-activity relationship for apoptolidin: selective functionalization of the hydroxyl group array.

Paul A Wender1, Orion D Jankowski, Elie A Tabet, Haruo Seto.   

Abstract

[reaction: see text] To investigate the structural basis for the exceptional selectivity and activity of apoptolidin (1), a strategy has been devised that allows for selective functionalization of seven of its eight hydroxyl groups based on progressive silyl protection, derivatization, and deprotection. The syntheses of these derivatives and their ability to inhibit F(0)F(1)-ATPase are reported.

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Year:  2003        PMID： 12583750     DOI： 10.1021/ol027366w

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


  11 in total

1.  Biosynthesis of the Apoptolidins in Nocardiopsis sp. FU 40.

Authors:  Yu Du; Dagmara K Derewacz; Sean M Deguire; Jesse Teske; Jacques Ravel; Gary A Sulikowski; Brian O Bachmann
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

Review 2.  Natural products and other inhibitors of F1FO ATP synthase.

Authors:  Bhargav A Patel; Terin L D'Amico; Brian S J Blagg
Journal:  Eur J Med Chem       Date:  2020-09-03       Impact factor: 6.514

3.  Fluorescent probes of the apoptolidins and their utility in cellular localization studies.

Authors:  Sean M DeGuire; David C Earl; Yu Du; Brenda A Crews; Aaron T Jacobs; Alessandro Ustione; Cristina Daniel; Katherine M Chong; Lawrence J Marnett; David W Piston; Brian O Bachmann; Gary A Sulikowski
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-27       Impact factor: 15.336

4.  Apoptolidins B and C: isolation, structure determination, and biological activity.

Authors:  Paul A Wender; Martin Sukopp; Kate Longcore
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

5.  Light-induced isomerization of apoptolidin a leads to inversion of C2-C3 double bond geometry.

Authors:  Brian O Bachmann; Ruth McNees; Bruce J Melancon; Victor P Ghidu; Rachel Clark; Brenda C Crews; Sean M Deguire; Lawrence J Marnett; Gary A Sulikowski
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

6.  Apoptolidins E and F, new glycosylated macrolactones isolated from Nocardiopsis sp.

Authors:  Paul A Wender; Kate E Longcore
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

7.  An approach to the site-selective diversification of apoptolidin A with peptide-based catalysts.

Authors:  Chad A Lewis; Kate E Longcore; Scott J Miller; Paul A Wender
Journal:  J Nat Prod       Date:  2009-10       Impact factor: 4.050

8.  Correlation of F0F1-ATPase inhibition and antiproliferative activity of apoptolidin analogues.

Authors:  Paul A Wender; Orion D Jankowski; Kate Longcore; Elie A Tabet; Haruo Seto; Taijiro Tomikawa
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

9.  Total synthesis of apoptolidin A.

Authors:  Michael T Crimmins; Hamish S Christie; Alan Long; Kleem Chaudhary
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

10.  Synthesis and evaluation of the cytotoxicity of apoptolidinones A and D.

Authors:  Victor P Ghidu; Jingqi Wang; Bin Wu; Qingsong Liu; Aaron Jacobs; Lawrence J Marnett; Gary A Sulikowski
Journal:  J Org Chem       Date:  2008-06-11       Impact factor: 4.354
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