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Sets of aldolase antibodies with antipodal reactivities, formal synthesis of epothilone e by large-scale antibody-catalyzed resolution of thiazole aldol

Academic Article
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Overview

authors

  • Sinha, Subhash
  • Sun, J.
  • Miller, G.
  • Barbas III, Carlos
  • Lerner, Richard

publication date

  • November 1999

journal

  • Organic Letters  Journal

abstract

  • [formula: see text] Three monoclonal aldolase antibodies, generated against a beta-diketone hapten by reactive immunization, catalyzed rapid and highly enantioselective retro-aldol reactions of ent-8a-k, providing optically pure 8a-k by kinetic resolution. Compounds (+/-)-8a, (+/-)-8g, and (+/-)-8k have been resolved in multigram quantities using 0.003, 0.005, and 0.0004 mol% antibody catalysts, respectively. Resolved compounds 8a-k are useful synthons for the construction of epothilones A-E (2-6) and their analogues. Here, a formal synthesis of epothilone E, 6 has been achieved starting from compound 8g.

subject areas

  • Antibodies, Catalytic
  • Antibodies, Monoclonal
  • Epothilones
  • Epoxy Compounds
  • Fructose-Bisphosphate Aldolase
  • Immunization
  • Thiazoles
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol990261h

PubMed ID

  • 10836025
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Additional Document Info

start page

  • 1623

end page

  • 1626

volume

  • 1

issue

  • 10

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