Aldolase catalyzed L-phenylserine synthesis in a slug-flow microfluidic system - Performance and diastereoselectivity studies

J. Čech, V. Hessel, M. Přibyl

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Abstract

We study synthesis of . L-phenylserine catalyzed by the enzyme . L-threonine aldolase in a slug-flow microfluidic system. Slug-flow arrangement allows for the continuous refilling of sparingly soluble substrate (benzaldehyde) into an aqueous reaction mixture. We identified suitable composition of an organic phase to provide stable slug-flow in a wide range of operational parameters. Solvent screening revealed that tert-butyl methyl ether (TBME) as the organic solvent provides the most friendly environment for . L-phenylserine synthesis due to a low degree of enzyme deactivation and high benzaldehyde concentration in the reaction mixture. The effects of substrate concentrations, enzyme concentration, and dimethylsulfoxide (DMSO) concentration on the . L-phenylserine concentration in the product stream were examined and proper reaction conditions were identified. Experimental results on the . L-phenylserine diastereoselectivity demonstrate that the amount of . syn-conformation of . L-phenylserine increases with the reaction time. High . syn- to . anti- concentration ratio is achieved with 2-methyltetrahydrofuran (MeTHF) solvent in a system with long residence time and, finally, low . syn- to . anti- concentration ratio is provided by toluene environment and short residence time.

Original languageEnglish
Pages (from-to)97-105
Number of pages9
JournalChemical Engineering Science
Volume169
DOIs
Publication statusPublished - 21 Sep 2017

Keywords

  • Enzyme
  • Microchip
  • Microfluidics
  • Phenylserine
  • Slug flow
  • Threonine aldolase

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