Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 11-12, Pages 1842-1848Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900218
Keywords
alcohol dehydrogenases; diols; hydrogen transfer; hydroxy ketones; quasi-irreversible reduction
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Regio- and stereoselective reductions of several diketones to afford enantiopure hydroxy ketones or diols were accomplished using isolated alcohol dehydrogenases (ADHs). Results could be rationalised taking into account different (Promiscuous) substrate-binding modes in the active site of the enzyme. Furthermore, interesting natural cyclic diketones were also reduced with high regio- and stereoselectivity. Some of the 1,2- and 1,3-diketones used in this study were reduced by employing a low excess of the hydrogen donor (2-propanol) due to the quasi-irreversibility of these ADH-catalysed processes. Thus, using lower quantities of co-substrate, scale-up could be easily achieved.
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