Improving Gluconobacter oxydans performance in the in situ removal of the inhibitor for asymmetric resolution of racemic 1-phenyl-1,2-ethanediol

Li, Dai-Huan; Lin, Jian; Wei, Dongzhi

doi:10.1016/j.biortech.2014.02.104

Cited by 8 publications

(5 citation statements)

References 19 publications

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“…The diols can be oxidized by some AAB strains, too. For example, 1,3-butandiol, 2,3- butandiol, (2R,3R)-2,3-butandiol, N -2-1,4-nonanodiol, 1,2-propanediol, ethanediol (ethylene glycol), racemical-1,2-butanediol, 1,3-propanediol and (R)-1-phenyl-1,2-ethanediol are oxidized to 3-hydroxybutyric acid [21] (Romano et al, 2002 ), (S)-acetoin [22] (Romano et al, 2002 ; Wang et al, 2013 ; Zhou et al, 2018 ), diacetyl [23] , γ-nonanoic lactone [24] (Romano et al, 2002 ), (R)-2-hydroxy-propionic acid ( d -(-)-lactic acid) [25] (Su et al, 2004 ), glycolic acid [26] (Wei et al, 2009 ), (R)-2-hydroxybutyric acid [27] (Gao et al, 2012 ), 3-hydroxypropionic acid [28] (Dishisha et al, 2015 ; Zhu et al, 2018 ), and (R)-mandelic acid [29] (Li et al, 2014 ), respectively.…”

Section: Natural Products Yielded By Aofmentioning

confidence: 99%

Oxidative Fermentation of Acetic Acid Bacteria and Its Products

Xie

Zhang

et al. 2022

Front. Microbiol.

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Acetic acid bacteria (AAB) are a group of Gram-negative, strictly aerobic bacteria, including 19 reported genera until 2021, which are widely found on the surface of flowers and fruits, or in traditionally fermented products. Many AAB strains have the great abilities to incompletely oxidize a large variety of carbohydrates, alcohols and related compounds to the corresponding products mainly including acetic acid, gluconic acid, gulonic acid, galactonic acid, sorbose, dihydroxyacetone and miglitol via the membrane-binding dehydrogenases, which is termed as AAB oxidative fermentation (AOF). Up to now, at least 86 AOF products have been reported in the literatures, but no any monograph or review of them has been published. In this review, at first, we briefly introduce the classification progress of AAB due to the rapid changes of AAB classification in recent years, then systematically describe the enzymes involved in AOF and classify the AOF products. Finally, we summarize the application of molecular biology technologies in AOF researches.

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Section: Natural Products Yielded By Aofmentioning

confidence: 99%

Oxidative Fermentation of Acetic Acid Bacteria and Its Products

Xie

Zhang

et al. 2022

Front. Microbiol.

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“…Gluconobacter oxydans DSM2003 was able to selectively oxidize the racemate to achieve (S)‐PED with yield of 40·8% under the optimum substrate concentration of 88 mmol l −1 without the addition of anion exchange resin (Li et al . ). The reports above showed the limitations of low substrate concentration and long reaction time.…”

Section: Introductionmentioning

confidence: 97%

“…Brevibacterium lutescens CCZU12-1 mentioned by He et al (2013) displayed the highest activity for the oxidation of (R)-PED leaving (S)-PED at the racemic substrate concentration of 50 mmol l À1 . Gluconobacter oxydans DSM2003 was able to selectively oxidize the racemate to achieve (S)-PED with yield of 40Á8% under the optimum substrate concentration of 88 mmol l À1 without the addition of anion exchange resin (Li et al 2014). The reports above showed the limitations of low substrate concentration and long reaction time.…”

Section: Introductionmentioning

confidence: 99%

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

Peng

Zhao

et al. 2019

Lett Appl Microbiol

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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.

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“…Chiral 1-phenyl-1,2-ethanediol (PED) plays an essential role in the synthesis of fine chemical compounds, pharmaceutical industry compounds, and liquid crystals (Cazetta et al, 2014;Li et al, 2014). The enantiomer (R)-PED is used as an important synthon for the fabrication of (R)-norfluoxetine, (R)-fluoxetine (Cui et al, 2017), and β-adrenergic blocking agents (Kamal et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

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

Peng

et al. 2020

Front. Bioeng. Biotechnol.

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phenyl-1,2-ethanediol is an important synthon for the preparation of β-adrenergic blocking agents. This study identified a (2R,3R)-butanediol dehydrogenase (KgBDH) from Kurthia gibsonii SC0312, which showed high enantioselectivity for production of (R)-1-phenyl-1,2-ethanediol by reduction of 2-hydroxyacetophenone. KgBDH was expressed in a recombinant engineered strain, purified, and characterized. It showed good catalytic activity at pH 6-8 and better stability in alkaline (pH 7.5-8) than an acidic environment (pH 6.0-7.0), providing approximately 73 and 88% of residual activity after 96 h at pH 7.5 and 8.0, respectively. The maximum catalytic activity was obtained at 45 • C; nevertheless, poor thermal stability was observed at >30 • C. Additionally, the examined metal ions did not activate the catalytic activity of KgBDH. A recombinant Escherichia coli strain coexpressing KgBDH and glucose dehydrogenase (GHD) was constructed and immobilized via entrapment with a mixture of activated carbon and calcium alginate via entrapment. The immobilized cells had 1.8-fold higher catalytic activity than that of cells immobilized by calcium alginate alone. The maximum catalytic activity of the immobilized cells was achieved at pH 7.5, and favorable pH stability was observed at pH 6.0-9.0. Moreover, the immobilized cells showed favorable thermal stability at 25-30 • C and better operational stability than free cells, retaining approximately 55% of the initial catalytic activity after four cycles. Finally, 81% yields (195 mM product) and >99% enantiomeric excess (ee) of (R)-1-phenyl-1,2-ethanediol were produced within 12 h through a fed-batch strategy with the immobilized cells (25 mg/ml wet cells) at 35 • C and 180 rpm, with a productivity of approximately 54 g/L per day.

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Improving Gluconobacter oxydans performance in the in situ removal of the inhibitor for asymmetric resolution of racemic 1-phenyl-1,2-ethanediol

Cited by 8 publications

References 19 publications

Oxidative Fermentation of Acetic Acid Bacteria and Its Products

Oxidative Fermentation of Acetic Acid Bacteria and Its Products

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

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

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