Highly selective resolution of racemic 1‐phenyl‐1,2‐ethanediol by a novel strain Kurthia gibsonii SC 0312

Abstract

Chiral 1‐phenyl‐1,2‐ethanediol (PED) performs vital effect for the preparation of pharmaceuticals, agrochemicals and cosmetics. In the study, a newly isolated strain Kurthia gibsoniiSC0312 with the ability to selectively oxidize racemic PED to achieve (S)‐PED was evaluated in the aqueous reaction system. The strain showed excellent catalytic performances within the range of pH 5·5–8·5, temperature 25–45°C and the amount of cell 15 mg ml−1 to 30 mg ml−1. Besides, 2‐hydroxyacetophenone (HAP) as the oxidation product displayed a stronger inhibition to the catalytic activity of cell, only remaining <63% of catalytic activity after incubation at 40 mmol l−1 HAP for 6 h. For various metal ions, Cu2+ can obviously improve 1·7 times of the catalytic activity of cell at the concentration of 0·2 mmol l−1. Acetone can stimulate the catalytic capacity of cell to improve the optical purity of (S)‐PED at the PED concentration of 80 mmol l−1, up to appropriately 94% from 85·4%; compared to the resting cell, growing cell exerted no positive effect in the yield and optical purity. Finally, a highly effective kinetic resolution system of racemic PED by the new strain was obtained, with the (S)‐PED yield of 41% and optical purity of 94%. Significance and Impact of the Study Biocatalyst is a vital component in the process of biotransformation. There are a growing number of studies of biocatalyst reporting the preparation of enantiomer of 1‐phenyl‐1,2‐ethanediol. And the performance of this preparation reaction is also gradually improving. This study is the first to demonstrate that Kurthia gibsonii can efficiently and selectively oxidize racemic 1‐phenyl‐1,2‐ethanediol, and we assess the effect of various factors on the catalytic performance of the strain. The work adds to a growing body of evidence for using biocatalytic method in the synthesis of chiral 1‐phenyl‐1,2‐ethanediol and provides a probable approach to mine excellent properties of enzymes.

Designing Modular Cell-free Systems for Tunable Biotransformation of l-phenylalanine to Aromatic Compounds

“…In this work, we aim to address the challenge by designing modular cell-free systems for tunable biotransformation, which can be used to convert the same precursor L-Phe to two value-added aromatic compounds without using the water-insoluble substrate styrene ( Figure 1 ). The first target compound is the chiral drug intermediate ( S )-1-phenyl-1,2-ethanediol (( S )-PED) and the second one is the rose-like fragrance 2-phenylethanol (2-PE) ( Peng et al, 2019 ; Wang et al, 2019 ). These two aromatic compounds share a common upstream intermediate styrene.…”

Identification and characterization of thermostable endo‐polygalacturonase II B from Aspergillus luchuensis

“…Temperature and pH are the two important parameters affecting the catalytic properties of the enzyme (Abdel‐Kareem & Zohri, ; Peng, Ou, Zhao, Zong, & Lou, ). The effects of temperature and pH on enzymatic properties of the recombinant PgaB were analyzed.…”

“…Temperature and pH are the two important parameters affecting the catalytic properties of the enzyme(Abdel-Kareem & Zohri, 2018;Peng, Ou, Zhao, Zong, & Lou, 2019). The effects of temperature andF I G U R E 2 Identification and expression of endo-polygalacturonase II B gene from Aspergillus luchuensis.…”

Immobilization of Cofactor Self-Sufficient Recombinant Escherichia coli for Enantioselective Biosynthesis of (R)-1-Phenyl-1,2-Ethanediol

“…Some alcohol dehydrogenases from microorganisms have been reported to asymmetrically reduce 2-hydroxyacetophenone (HAP) to (R)-PED (Chen et al, 2015;Sudhakara and Chadha, 2017). Kurthia gibsonii SC0312 (K. gibsonii SC0312) isolated by our group is able to prepare chiral PED with high enantioselectivity (Peng et al, 2019). Nevertheless, the functional enzymes from K. gibsonii SC0312 for the preparation of chiral PED were yet unknown.…”