A practical chemoenzymatic synthesis of an LTD4 antagonist

D. L. Hughes, Z. Song, G. B. Smith, J. J. Bergan, G. C. Dezeny, E. J.J. Grabowski, P. J. Reider

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

Enzymatic asymmetrization of a prochiral diester having 4 bonds between the ester group and prochiral center is the cornerstone of a short and efficient synthesis of an LTD4 antagonist. The enzymatic hydrolysis occurs in a heterogeneous slurry, but a kinetic analysis shows that the reaction takes place in solution. Product inhibition of the enzyme is severe, requiring that a substantial amount of enzyme be used relative to substrate. To more efficiently use the expensive enzyme, it was immobilized on several supports, the most effective of which was XAD 7 with crosslinked enzyme.

Original languageEnglish (US)
Pages (from-to)865-874
Number of pages10
JournalTetrahedron: Asymmetry
Volume4
Issue number5
DOIs
StatePublished - May 1993
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Hughes, D. L., Song, Z., Smith, G. B., Bergan, J. J., Dezeny, G. C., Grabowski, E. J. J., & Reider, P. J. (1993). A practical chemoenzymatic synthesis of an LTD4 antagonist. Tetrahedron: Asymmetry, 4(5), 865-874. https://doi.org/10.1016/S0957-4166(00)80124-X