Efficient kinetic resolution of (RS)‐1‐phenylethanol by a mycelium‐bound lipase from a wild‐type Aspergillus oryzae strain

Abstract

A mycelium-bound lipase from Aspergillus oryzae (AOL) exhibited excellent enantioselectivity for kinetic resolution of (RS)-1-phenylethanol ((RS)-1-PE) in organic solvent. The various reaction parameters affecting the conversion and enantioselectivity were studied, including type of acyl donor, solvent, molar ratio, temperature, enzyme amount, and substrate concentration. The optimum reaction conditions were found to be transesterification with vinyl acetate at 30 °C in methyl tert-butyl ether with a vinyl acetate: (RS)-1-PE molar ratio of 1:1 and an enzyme concentration of 60 g/L. At the optimum reaction conditions, the conversion could reach above 46% with >99% enantiomeric excess of the product, (R)-1-phenylethyl acetate, when the substrate concentration was below 1.4 M. The enzyme displayed an excellent enantioselectivity with an E-value of >200 and a strong tolerance for high substrate concentration of up to 1.8 M. Those results indicated that AOL was a promising biocatalyst in the kinetic resolution of (RS)-1-PE.

Surfactant-modified Aspergillus oryzae lipase as a highly active and enantioselective catalyst for the kinetic resolution of (RS)-1-phenylethanol

“…The optimal temperature was lower than that of the native lipase (Yan et al 2017). Wu et al also discovered that the LSC displayed a lower optimal temperature than the native one (Wu et al 2004).…”

“…The LSC prepared with tetrahydrofuran (THF) as a cosolvent exhibited the highest activity in resolution of (RS)-1-PE, giving a conversion of 46.8% with a reaction time of 2 h. The activity of the LSC was significantly higher than that of natural lipase (myceliumbound lipase). The natural lipase required about 24 h to achieve the same conversion rate (Yan et al 2017). The LSC prepared without an organic cosolvent likewise displayed a higher conversion of 31.6% with the same reaction time (at 2 h of reaction).…”

“…The lipase from Aspergillus oryzae (AOL) has been proven as being a versatile biocatalyst. It can be used in the kinetic resolution of a biotin intermediate lactone (Zheng et al 2009), α-lipoic acid (Yan et al 2009) and 1-phenylethanol (Yan et al 2017). It can also stereoselectively catalyze the hydrolysis of ethyl 2-(4-hydroxyphenoxy) propanoate and its analogues, which are key intermediates in the synthesis of aryloxyphenoxy propionate herbicides (Zheng et al 2013).…”

Protective effects of scopolamine and penehyclidine hydrochloride on acute cerebral ischemia-reperfusion injury after cardiopulmonary resuscitation and effects on cytokines

“…This is especially true for older patients with significantly declined body functions that result in high sensitivity and poor tolerance to hypoxia. It was confirmed that ( 3 , 4 ) both spontaneous respiration and the heartbeat can be restored in some older patients with cardiac and respiratory arrest, if it is detected early, and treated immediately and appropriately. Early detection and immediate and appropriate treatment can reduce the impact of respiratory and cardiac arrest on the functions of key organs, and is therefore the key to a successful rescue.…”