4.4 Article

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

Journal

TETRAHEDRON LETTERS
Volume 42, Issue 25, Pages 4131-4133

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)00694-3

Keywords

eicosanoids; epoxides; inversion reactions; asymmetric synthesis; biosynthesis

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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. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

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