One-pot biotransformation of racemic styrene oxide into (R)-1,2-phenylethandiol by two recombinant microbial epoxide hydrolases

Abstract

An enantioconvergent biotransformation of racemic styrene oxide by using two recombinant microbial epoxide hydrolases (EHs) in one pot has been investigated to prepare enantiopure vicinal diols. The recombinant whole cell possessing EH gene from ^ëéÉêÖáääìë= åáÖÉê LK or= oÜçÇçíçêìä~= Öäìíáåáë exhibited a complementary enantioselectivity and regioselectivity, compared to the recombinant cell containing `~ìäçÄ~ÅíÉê=ÅêÉëÅÉåíìë EH gene. When two recombinant microbial EHs were used in combination, 1.3 g of enantiopure (o)-1,2-phenylethandiol with more than 90% enantiopurity and 95% overall yield was obtained from 1.2 g of racemic styrene oxide in a preparative-scale batch enantioconvergent biotransformation. © KSBB hÉóïçêÇëW=Éå~åíáçÅçåîÉêÖÉåí=Äáçíê~åëÑçêã~íáçåI=Éå~åíáçéìêÉ=ÇáçäI=ãáÅêçÄá~ä=ÉéçñáÇÉ=ÜóÇêçä~ëÉI=êÉÅçãÄáå~åí=ïÜçäÉJÅÉää= = ÄáçÅ~í~äóëí= = = = =

Inverting hydrolases and their use in enantioconvergent biotransformations

“…One-pot processes with two enantiocomplementary epoxide hydrolases (Figure 2, type 2) have recently been developed for the production of ( R )-phenyl-1,2-ethanediol using enzyme pairs from A. niger LK/ Rhodotorula glutinis [25] and C. crescentus / Mugil cephalus [26] with >90% ee and conversion. High selectivity and conversion were also obtained when two enzymes from the Neocarzinostatin gene cluster were combined in a biocatalytic deracemization protocol [55].…”

Optimization of the enzymatic one pot reaction for the synthesis of uridine 5′-diphosphogalactose

“…In this study, we attempted to employ an approach using recombinant cell extracts for the synthesis of UDP-Gal for galactosyltransferase, which can be utilized to synthesize various disaccharides and oligosaccharides [11]. In particular, we focused on the optimization of the multienzyme reaction for UDP-Gal synthesis, and the analysis of its rate-determining to improve the yield of UDP-Gal [12]. …”

Synthesis of enantiomerically pure alcohols and amines via biocatalytic deracemisation methods

“…Further examples with isolated enzymes have been reported ever since. 123 , 124 An interesting alternative to the aforementioned bienzymatic EH-based deracemisation processes is to use EHs acting on both enantiomers of an oxirane albeit in Markovnikov and anti -Markovnikov selectivity. Next to the example by Furstoss and coworkers using the EH from Solanum tuberosum ( St EH, Scheme 33 ), 125 further EHs and their use in corresponding single enzymatic enantioconvergent reactions have been reported.…”