Control of enantioselectivity in the enzymatic reduction of halogenated acetophenone analogs by substituent positions and sizes

Koesoema, Afifa Ayu; Standley, Daron M.; Ohshima, Shusuke; Tamura, Masahito; Matsuda, Tomoko

doi:10.1016/j.tetlet.2020.151820

Cited by 12 publications

(4 citation statements)

References 33 publications

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“…Several enzymes associated with oxidation reactions have been applied by pharmaceutical and chemical industries for the oxidation of alcohols, sulfides, aldehydes, Baeyer–Villiger oxidation, and hydroxylation [ 122 , 123 , 124 , 125 , 126 , 127 ]. G. candidum was discovered to produce dehydrogenases with broad applications in organic synthesis [ 125 , 128 , 129 , 130 , 131 , 132 , 133 , 134 ]. For instance, G. candidum NBRC 4597 (GcAPRD) was discovered to produce a novel alcohol dehydrogenase (ALDH), acetophenone reductase, an enzyme with broad spectrum activity regarding the oxidation of aldehydes to carboxylic acids and selective activity for the oxidation of dialdehydes to aldehydic acids [ 129 , 135 , 136 ].…”

Section: Production Of Enzymes With Industrial Interestmentioning

confidence: 99%

“…G. candidum was discovered to produce dehydrogenases with broad applications in organic synthesis [ 125 , 128 , 129 , 130 , 131 , 132 , 133 , 134 ]. For instance, G. candidum NBRC 4597 (GcAPRD) was discovered to produce a novel alcohol dehydrogenase (ALDH), acetophenone reductase, an enzyme with broad spectrum activity regarding the oxidation of aldehydes to carboxylic acids and selective activity for the oxidation of dialdehydes to aldehydic acids [ 129 , 135 , 136 ]. This process has important agrochemical and pharmaceutical applications, but there are still limitations on its use due to its limited recyclability [ 137 ].…”

Section: Production Of Enzymes With Industrial Interestmentioning

confidence: 99%

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Uncovering the Biotechnological Importance of Geotrichum candidum

Kamilari

Stanton

Reen

et al. 2023

Foods

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Fungi make a fundamental contribution to several biotechnological processes, including brewing, winemaking, and the production of enzymes, organic acids, alcohols, antibiotics, and pharmaceuticals. The present review explores the biotechnological importance of the filamentous yeast-like fungus Geotrichum candidum, a ubiquitous species known for its use as a starter in the dairy industry. To uncover G. candidum’s biotechnological role, we performed a search for related work through the scientific indexing internet services, Web of Science and Google Scholar. The following query was used: Geotrichum candidum, producing about 6500 scientific papers from 2017 to 2022. From these, approximately 150 that were associated with industrial applications of G. candidum were selected. Our analysis revealed that apart from its role as a starter in the dairy and brewing industries, this species has been administered as a probiotic nutritional supplement in fish, indicating improvements in developmental and immunological parameters. Strains of this species produce a plethora of biotechnologically important enzymes, including cellulases, β-glucanases, xylanases, lipases, proteases, and α-amylases. Moreover, strains that produce antimicrobial compounds and that are capable of bioremediation were identified. The findings of the present review demonstrate the importance of G. candidum for agrifood- and bio-industries and provide further insights into its potential future biotechnological roles.

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Section: Production Of Enzymes With Industrial Interestmentioning

confidence: 99%

Section: Production Of Enzymes With Industrial Interestmentioning

confidence: 99%

Uncovering the Biotechnological Importance of Geotrichum candidum

Kamilari

Stanton

Reen

et al. 2023

Foods

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“…The enantioselectivity excess (ee) values and the absolute congurations of 1b, 5b, and 6b were determined by comparing their GC retention times with the corresponding authentic samples prepared before. 35 Meanwhile, for 2b-4b and 7b, the reaction mixtures were extracted by dichloromethane, dried over MgSO 4 , and used for propionylation by propionyl chloride reaction. ee values and absolute congurations were determined by comparing the GC retention times of propionates of 2b-4b and 7b with the corresponding authentic samples prepared before.…”

Section: Micromole Scale Asymmetric Reduction Of Ketones By Gcaprd Nanocrystalmentioning

confidence: 99%

“…Previously prepared alcohol (4b-7b) and chiral ester (2b-4b and 7b) standards were used in this study. [33][34][35]…”

Section: Introductionmentioning

confidence: 99%

Organic–inorganic nanocrystal reductase to promote green asymmetric synthesis

2020

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Chemoenzymatic Asymmetric Synthesis of Pyridine‐Based α‐Fluorinated Secondary Alcohols

et al. 2021

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Dedicated to Professor Udo Kragl on the occasion of his 60th birthday.Fluoro-substituted and heteroaromatic compounds are valuable intermediates for a variety of applications in pharma-and agrochemistry and synthetic chemistry. This study investigates the chemoenzymatic preparation of chiral alcohols bearing a heteroaromatic ring with an increasing degree of fluorination in α-position. Starting from readily available picoline derivatives prochiral α-halogenated acyl moieties were introduced with excellent selectivity and 64-95 % yield. The formed carbonyl group was subsequently reduced to the corresponding alcohols using the alcohol dehydrogenase from Lactobacillus kefir, yielding an enantiomeric excess of 95-> 99 % and up to 98 % yield.

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Control of enantioselectivity in the enzymatic reduction of halogenated acetophenone analogs by substituent positions and sizes

Cited by 12 publications

References 33 publications

Uncovering the Biotechnological Importance of Geotrichum candidum

Uncovering the Biotechnological Importance of Geotrichum candidum

Organic–inorganic nanocrystal reductase to promote green asymmetric synthesis

Chemoenzymatic Asymmetric Synthesis of Pyridine‐Based α‐Fluorinated Secondary Alcohols

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