Stereoselective oxidation of racemic 1-arylethanols by basil cultured cells of Ocimum basilicum cv. Purpurascens

Itoh, Ken‐ichi; Nakamura, Kaoru; Utsukihara, Takamitsu; Sakamaki, Hiroshi; Horiuchi, C. Akira

doi:10.1007/s10529-007-9615-z

Cited by 5 publications

(4 citation statements)

References 19 publications

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“…Since the indan-1-one reduction efficiency by means of comminuted plants was so very low, we tried to transform the corresponding racemic alcohol. Stereoselective oxidation of alcohols has useful applications in organic synthesis, but it is less popular than the reduction of ketones in biotransformations [13]. So far, biooxidation has been described almost exclusively for model substrates such as 1-phenylethanol and its derivatives.…”

Section: Oxidation Of Indan-1-ol Using the Plant Enzyme Systemmentioning

confidence: 99%

“…In the biological approaches using biocatalysts, optically active alcohols are prepared from prochiral ketones [8][9][10][11], or racemic alcohols as starting materials [8,[12][13][14][15]. Biocatalytic desymmetrization using ketones is highly significant in several processes, as this allows one to obtain pure enantiomer in a 100% theoretical yield.…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11][19][20][21][22][23][24][25]. Biooxidation of alcohols has been described much less [8,[12][13][14][15]22].…”

Section: Introductionmentioning

confidence: 99%

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Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

et al. 2019

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The main purpose of this work was to discover the way to obtain pure enantiomers of indan-1-ol. The subject of the study was the ability of the plant enzyme system to reduce the carbonyl group of indan-1-one, as well as to oxidize the hydroxyl group of racemic indan-1-ol. Locally available fruit and vegetables were selected for stereoselective biotransformation. During the reduction, mainly alcohol of the S-(+)-configuration with a high enantiomeric excess (ee = 99%) was obtained. The opposite enantiomer was obtained in bioreduction with the apple and parsley. Racemic indan-1-ol was oxidized by all catalysts. The best result was obtained for the Jerusalem artichoke: Over 50% conversion was observed after 1 h, and the enantiomeric excess of unreacted R-(–)-indan1-ol was 100%.

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Section: Oxidation Of Indan-1-ol Using the Plant Enzyme Systemmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

et al. 2019

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“…It is used as a flavorant in food, perfumery, cosmetics and medicines [9]. There are some reports of biotransformation of chemical compounds with O. basilicum culture [10]. Azadirachta indica A. Juss.…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of oral contraceptive ethynodiol diacetate with microbial and plant cell cultures

Zafar

Yousuf

Kayani

et al. 2012

Chemistry Central Journal

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BackgroundBiotransformation by using microbial and plant cell cultures has been applied effectively for the production of fine chemicals on large scale. Inspired by the wealth of literature available on the biotransformation of steroids, we decided to investigate the biotransformation of ethynodiol diacetate (1) by using plant and microbial cultures.ResultsThe biotransformation of ethynodiol diacetate (1) with Cunninghamella elegans and plant cell suspension cultures of Ocimum basilicum and Azadirachta indica is being reported here for the first time. Biotransformation of 1 with Cunninghamella elegans yielded three new hydroxylated compounds, characterized as 17α-ethynylestr-4-en-3β,17β-diacetoxy-6α-ol (2), 17α-ethynylestr-4-en-3β,17β-diacetoxy-6β-ol (3), and 17α-ethynylestr-4-en-3β,17β-diacetoxy-10β-ol (4) and a known metabolite, 17α-ethynyl-17β-acetoxyestr-4-en-3-one (5). The biotransformation of 1 with Ocimum basilicum included hydrolysis of the ester group, oxidation of alcohol into ketone, and rearrangement of the hydroxyl group. Thus four major known metabolites were characterized as 17α-ethynyl-17β-acetoxyestr-4-en-3-one (5), 17α-ethynyl-17β-hydroxyestr-4-en-3-one (6), 17α-ethynyl-3 β-hydroxy-17β-acetoxyestr-4-ene (7) and 17α-ethynyl-5α,17β-dihydroxyestr-3-ene (8). Biotransformation of 1 with Azadirachta indica culture yielded compounds 5 and 6. Spectroscopic data of compound 8 is being reported for the first time. Structure of compound 6 was unambiguously deduced through single-crystal x-ray diffraction studies.ConclusionBiotransformation of an oral contraceptive, ethynodiol diacetate (1), by using microbial and plant cell cultures provides an efficient route to the synthesis of a library of new steroids with potential contraceptive properties. These methods can be employed in the production of such compounds with high stereoselectivity.

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Towards the discovery of alcohol dehydrogenases: NAD(P)H fluorescence-based screening and characterization of the newly isolated Rhodococcus erythropolis WZ010 in the preparation of chiral aryl secondary alcohols

Yang

Ying

et al. 2012

Journal of Industrial Microbiology and Biotechnology

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A simple and reliable procedure was developed to screen biocatalysts with high alcohol dehydrogenase activity, efficient internal coenzyme regeneration, and high stereoselectivity. The strategy of activity screening in a microtitre plate format was based on the detection of fluorescence of NAD(P)H originating from the oxidation of alcohols. The primary and secondary screenings from soil samples yielded a versatile bacterial biocatalyst Rhodococcus erythropolis WZ010 demonstrating potential for the preparation of chiral aryl secondary alcohols. In terms of activity and stereoselectivity, the optimized reaction conditions in the stereoselective oxidation were 30 °C, pH 10.5, and 250 rpm, whereas bioreduction using glucose as co-substrate was the most favorable at 35 °C and pH 7.5 in the static reaction mixture. Under the optimized conditions, fresh cells of the strain stereoselectively oxidized the (S)-enantiomer of racemic 1-phenylethanol (120 mM) to acetophenone and afforded the unoxidized (R)-1-phenylethanol in 49.4 % yield and >99.9 % enantiomeric excess (e.e.). In the reduction of 10 mM acetophenone, the addition of 100 mM glucose significantly increased the conversion rate from 3.1 to 97.4 %. In the presence of 800 mM glucose, acetophenone and other aromatic ketones (80 mM) were enantioselectively reduced to corresponding (S)-alcohols with excellent e.e. values. Both stereoselective oxidation and asymmetric reduction required no external cofactor regeneration system.

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Stereoselective oxidation of racemic 1-arylethanols by basil cultured cells of Ocimum basilicum cv. Purpurascens

Cited by 5 publications

References 19 publications

Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

Plant-Mediated Enantioselective Transformation of Indan-1-One and Indan-1-ol

Biotransformation of oral contraceptive ethynodiol diacetate with microbial and plant cell cultures

Towards the discovery of alcohol dehydrogenases: NAD(P)H fluorescence-based screening and characterization of the newly isolated Rhodococcus erythropolis WZ010 in the preparation of chiral aryl secondary alcohols

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