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

31 Citations (Scopus)

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

Fingerprint

Enantiomers
Linoleic Acid
Cytochromes
Arachidonic Acid
Acids
14,15-epoxy-5,8,11-eicosatrienoic acid
leukotoxin
vernolic acid

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Falck, J. R., Reddy, Y. K., Haines, D. C., Reddy, K. M., Krishna, U. M., Graham, S., ... 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

Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid). / Falck, J R; Reddy, Y. Krishna; Haines, Donovan C.; Reddy, Komandla Malla; Krishna, U. Murali; Graham, Sandra; Murry, Barbara; Peterson, Julian A.

In: Tetrahedron Letters, Vol. 42, No. 25, 18.06.2001, p. 4131-4133.

Research output: Contribution to journalArticle

Falck, JR, Reddy, YK, Haines, DC, Reddy, KM, Krishna, UM, Graham, S, Murry, B & Peterson, JA 2001, 'Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)', Tetrahedron Letters, vol. 42, no. 25, pp. 4131-4133. https://doi.org/10.1016/S0040-4039(01)00694-3
Falck, J R ; Reddy, Y. Krishna ; Haines, Donovan C. ; Reddy, Komandla Malla ; Krishna, U. Murali ; Graham, Sandra ; Murry, Barbara ; Peterson, Julian A. / Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid). In: Tetrahedron Letters. 2001 ; Vol. 42, No. 25. pp. 4131-4133.
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AU - Murry, Barbara

AU - Peterson, Julian A.

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