Promiscuous substrate binding explains the enzymatic stereoand regiocontrolled synthesis of enantiopure hydroxy ketones and diols

  • Kurina-Sanz M
  • Bisogno F
  • Lavandera I
 et al. 
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Abstract

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.

Author-supplied keywords

  • Alcohol dehydrogenases
  • Diols
  • Hydrogen transfer
  • Hydroxy ketones
  • Quasi-irreversible reduction

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