Hydroxynitrile lyase catalyzed cyanohydrin synthesis at high pH-values

Bioprocess and Biosystems Engineering
Jan von LangermannUdo Kragl

Abstract

The application of unusual high pH-values within enzymatic cyanohydrin synthesis has been investigated. Usually enzymatic cyanohydrin synthesis in two-phase systems requires low pH-values within the aqueous phase to suppress the non-enzymatic side reaction. In contrast, we investigated the usage of pH-values above pH 6 by using the highly enantioselective (S)-selective hydroxynitrile lyase from Manihot esculenta. With these unusual reaction conditions also the unfavorable substrate 3-phenoxy-benzaldehyde can be converted by the wild type enzyme with excellent conversion and enantiomeric excess yielding pure (S)-3-phenoxy-benzaldehyde cyanohydrin with an enantiomeric excess of 97%. Although the variant MeHNL-W128A shows a higher activity with respect to this reaction, the enantioselectivity was reduced (85% e.e.(S)). Additionally, a new continuous spectroscopic cyanohydrin assay monitoring the formation of 3-phenoxy-benzaldehyde cyanohydrin was developed.

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Citations

Mar 21, 2008·Bioprocess and Biosystems Engineering·Dirk Weuster-Botz
Jun 4, 2013·Applied and Environmental Microbiology·Kathrin Emmi ScholzUlrich Krauss
Mar 2, 2012·Chembiochem : a European Journal of Chemical Biology·Daniel OkrobMartina Pohl
Jun 11, 2016·Organic & Biomolecular Chemistry·Paula BraccoUlf Hanefeld
Jan 31, 2013·Chemical Society Reviews·Ulf Hanefeld
Nov 5, 2020·Chembiochem : a European Journal of Chemical Biology·Yu-Cong ZhengJian-He Xu
Mar 23, 2011·Chemical Reviews·Margarita BrovettoGustavo A Seoane

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