Enantioconvergent bioconversion of p-chlorostyrene oxide to (R)-p-chlorophenyl-1,2-ethandiol by the bacterial epoxide hydrolase of Caulobacter crescentus

Abstract

The enantioselective hydrolysis of eight racemic styrene oxide derivatives has been investigated by using the recombinant cell containing epoxide hydrolase (EH) of Caulobacter crescentus. Some styrene oxide derivatives were hydrolyzed via enantioconvergent manner so that enantiopure diol products could be prepared with a 100% theoretical yield. The recombinant cell containing C. crescentus EH exhibited an ability to hydrolyze racemic p-chlorostyrene oxide the most enantioconvergently, thus affording the formation of the corresponding (R)-diol with enantiomeric excess (ee) as high as 95% and a 72% yield in preparative-scale (16.8 g/l) bioconversion.

The effect of deep eutectic solvents on the asymmetric hydrolysis of styrene oxide by mung bean epoxide hydrolases

“…There is no doubt that chiral pure epoxides and vicinal diols have an important role in the synthesis of pharmaceuticals, pesticides and cosmetics (Hwang et al 2008;Kotik et al 2005;Xu et al 2006). Glycidyl phenyl ether is a vital drug intermediate for the preparing aryloxy propanolamines (Bala et al 2010).…”

Recent developments in the asymmetric hydrolytic ring opening of epoxides catalysed by microbial epoxide hydrolase

“…In a similar manner, the enantioconvergent biohydrolysis of styrene oxide 1 using the bacterial epoxide hydrolase from C. crescentus 47 provides the corresponding diol in 90% ee.…”

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

“…Based on the above approach, the regioselectivity coefficient of CCEH, ANEH, and RGEH toward racemic styrene oxide was determined. Previously, recombinant CCEH was shown to attack predominantly (S)-styrene oxide at α carbon atom [14]. On the contrary, it was shown that recombinant ANEH and RGEH preferentially hydrolyzed (R)-styrene oxide predominantly into (R)-1,2-phenylethandiol with the retention of configuration (Table 1).…”

“…A novel marine fish EH gene from Mugil cephalus has been also cloned and characterized [12]. Recently, we have explored the enantioconvergent hydrolysis of racemic styrene oxide based on the enantio-flexibility of the C. crescentus EH (CCEH) and M. cephalus EH (MCEH) [13,14]. However, the MCEH could not be used in a preparative-scale biotransformation because of their low availability.…”