Journal of the American Chemical Society p. 4800 - 4808 (1983)
Update date:2022-08-03
Topics:
Schwab
Li
Thomas
Cyclohexane oxygenase, from Acinetobacter NCIB 9871, has been incubated with (2S,6S)- left bracket 2,6-**2H//2 right bracket - and (2R)- left bracket 2-**2H//1 right bracket cyclohexanone. The resulting labeled epsilon -caprolactone (2-oxepanone) samples were degraded to 1-pentanol, which was esterified by using ( minus )-camphanyl chloride. Analysis of the camphanates by deuterium NMR spectroscopy, using Eu(dpm)//3, showed that the conversion of ketone to lactone had in each case proceeded with complete retention of configuration at the migrating carbon center. A similar degradation of (2R)- left bracket 2-**2H//1 right bracket cyclohexanone itself showed that reduction of left bracket 2-**2H//1 right bracket -cyclohex-2-enone by Beauveria bassiana ATCC 7159 is also completely stereoselective. A method has been developed for assessing the enantioselectivity of enzymes toward racemic substrate mixtures.
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