Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

J R Falck, Y. Krishna Reddy, Donovan C. Haines, Komandla Malla Reddy, U. Murali Krishna, Sandra Graham, Barbara Murry, Julian A. Peterson

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S),15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion.

Original languageEnglish (US)
Pages (from-to)4131-4133
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number25
DOIs
StatePublished - Jun 18 2001

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Keywords

  • Asymmetric synthesis
  • Biosynthesis
  • Eicosanoids
  • Epoxides
  • Inversion reactions

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Falck, J. R., Reddy, Y. K., Haines, D. C., Reddy, K. M., Krishna, U. M., Graham, S., Murry, B., & Peterson, J. A. (2001). Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid). Tetrahedron Letters, 42(25), 4131-4133. https://doi.org/10.1016/S0040-4039(01)00694-3