Cinelli, Maris A.; Yang, Jun; Scharmen, Amy; Woodman, Joey; Karchalla, Lalitha M.; Stephen Lee, Kin Sing published the artcile< Enzymatic synthesis and chemical inversion provide both enantiomers of bioactive epoxydocosapentaenoic acids>, Quality Control of 699-12-7, the main research area is Enzymic synthesis epoxydocosapentaenoic acids Bacillus megaterium; chemoenzymatic synthesis; cytochrome P450; docosahexaenoic acid; epoxide inversion; epoxy fatty acids; lipids/chemistry; polyunsaturated fatty acids.
Epoxy PUFAs are endogenous cytochrome P 450 (P 450) metabolites of dietary PUFAs. Although these metabolites exert numerous biol. effects, attempts to study their complex biol. have been hampered by difficulty in obtaining the epoxides as pure regioisomers and enantiomers. To remedy this, we synthesized 19,20- and 16,17-epoxydocosapentaenoic acids (EDPs) (the two most abundant EDPs in vivo) by epoxidation of DHA with WT and the mutant (F87V) P 450 enzyme BM3 from Bacillus megaterium. WT epoxidation yielded a 4:1 mixture of 19,20:16,17-EDP exclusively as (S,R) enantiomers. Epoxidation with the mutant (F87V) yielded a 1.6:1 mixture of 19,20:16,17-EDP; the 19,20-EDP fraction was ∼9:1 (S,R):(R,S), but the 16,17-EDP was exclusively the (S,R) enantiomer. To access the (R,S) enantiomers of these EDPs, we used a short (four-step) chem. inversion sequence, which utilizes 2-(phenylthio)ethanol as the epoxide-opening nucleophile, followed by mesylation of the resulting alc., oxidation of the thioether moiety, and base-catalyzed elimination. This short synthesis cleanly converts the (S,R)-epoxide to the (R,S)-epoxide without loss of enantiopurity. This method, also applicable to eicosapentaenoic acid and arachidonic acid, provides a simple, cost-effective procedure for accessing larger amounts of these metabolites.
Journal of Lipid Research published new progress about Bacillus megaterium. 699-12-7 belongs to class alcohols-buliding-blocks, and the molecular formula is C8H10OS, Quality Control of 699-12-7.
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