Journal of Organic Chemistry p. 3960 - 3966 (1983)
Update date:2022-08-02
Topics:
Wilson, William K.
Baca, Shawn B.
Barber, Yolanda J.
Scallen, Terence J.
Morrow, Cary J.
Pig liver esterase has been shown to stereoselectively hydrolyze the R enantiomer of several chiral 3-hydroxy-3-methylalkanoic acid esters of the form RC(Me)(OH)CH2COOR', where R = Et, CH2=CHCH2, Me(CH2)5, (MeO)2CHCH2, and PhCH2OCH2CH2 and R'= Me or Et.The unhydrolyzed ester and the reesterified carboxylic acid were analyzed for enantiomeric purity by NMR using the chiral shift reagent Eu(hfc)3.For the compounds studied, the S enantiomers consistently showed greater induced shifts.Products of the resolution are potential intermediates in the preparation of compactin analogues having defined stereochemistry at carbon-3.These analogues will be useful in testing the hypothesis that the hypocholesterolemic activity of compactin and its analogues resides in their ability to mimic the binding of mevaldic acid coenzyme A hemithioacetal to HMG-CoA reductase but not be reduced to mevalonate.
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