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Issue 25, 2012
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Investigation of asymmetric alcohol dehydrogenase (ADH) reduction of acetophenone derivatives: effect of charge density

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Abstract

In an effort to study the effect of substituent groups of the substrate on the alcohol dehydrogenase (ADH) reductions of aryl–alkyl ketones, several derivatives of acetophenone have been evaluated against ADHs from Lactobacillus brevis (LB) and Thermoanaerobacter sp. (T). Interestingly, ketones with non-demanding (neutral) para-substituents were reduced to secondary alcohols by these enzymes in enantiomerically pure form whereas those with demanding (ionizable) substituents could not be reduced. The effect of substrate size, their solubility in the reaction medium, electron donating and withdrawing properties of the ligand and also the electronic charge density distribution on the substrate molecules have been studied and discussed in detail. From the results, it is observed that the electronic charge distribution in the substrate molecules is influencing the orientation of the substrate in the active site of the enzyme and hence the ability to reduce the substrate.

Graphical abstract: Investigation of asymmetric alcohol dehydrogenase (ADH) reduction of acetophenone derivatives: effect of charge density

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Publication details

The article was received on 07 Nov 2011, accepted on 30 Apr 2012 and first published on 01 May 2012


Article type: Paper
DOI: 10.1039/C2OB06870B
Citation: Org. Biomol. Chem., 2012,10, 4961-4967
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    Investigation of asymmetric alcohol dehydrogenase (ADH) reduction of acetophenone derivatives: effect of charge density

    H. G. Naik, B. Yeniad, C. E. Koning and A. Heise, Org. Biomol. Chem., 2012, 10, 4961
    DOI: 10.1039/C2OB06870B

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