engleski

Stereoselective synthesis of chiral 1, 2-diols from (S)-2-hydroxypropiophenone by alcohol and glycerol dehydrogenases with coenzyme regeneration

The study describes enantioselective reduction of (S)-2-hydroxypropiophenone ((S)-2-HPP) to (1S, 2S)-1-phenylpropane-1, 2-diol ((1S, 2S)-1-PPD) mediated by alcohol dehydrogenase (LbADH) from Lactobacillus brevis and (1R, 2S)-1- phenylpropane- 1, 2-diol ((1R, 2S)-1-PPD) by glycerol dehydrogenase (GDH) from Cellulomonas sp.. As these dehydrogenases require the presence of NADH, the coenzyme regeneration was performed with formate dehydrogenase (FDH) from Candida boidinii. The chiral 1, 2-diol syntheses combined with coenzyme regeneration were carried out in repetitive batch reactors. Fresh (S)-2-HPP substrate was added three times during the repetitive experiments. All three enzymes were kinetically characterized and the kinetics of all reactions was determined. Based on results kinetic models for synthesis of both chiral 1, 2- diols for systems with and without coenzyme regeneration were developed and then combined with reactor mass balance equations. The proposed mathematical models were validated in a batch reactor. The developed models were in good agreement with the experimental data. For the system without coenzyme regeneration the equilibrium conversions of 60% and 34% using LbADH and GDH, respectively, were achieved. With coenzyme regeneration complete (S)-2-HPP conversions using both enzymes were achieved.

alcohol dehydrogenase ; glycerol dehydrogenase ; coenzyme regeneration ; (S)-2-hydroxypropiophenone ; mathematical modeling

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