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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F17%3A43913823" target="_blank" >RIV/60461373:22340/17:43913823 - isvavai.cz</a>

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0009250916304626?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0009250916304626?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.ces.2016.08.033" target="_blank" >10.1016/j.ces.2016.08.033</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

20402 - Chemical process engineering

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemical Engineering Science

ISSN

0009-2509

e-ISSN

—

Svazek periodika

169

Číslo periodika v rámci svazku

SI

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

97-105

Kód UT WoS článku

000405254800007

EID výsledku v databázi Scopus

2-s2.0-85008929511