Recent progress in biocatalysis for asymmetric oxidation and reduction

Matsuda, Tomoko; Yamanaka, Rio; Nakamura, Kaoru

doi:10.1016/j.tetasy.2008.12.035

Cited by 364 publications

(172 citation statements)

References 179 publications

(121 reference statements)

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“…In this context, bioreduction processes are often impressive due to the unmatched enantioselectivity of the enzymes in the case of generating chiral alcohols [12]. For the biocatalyzed reduction of fluorinated ketones, catalyst systems have been reported, including whole-cell systems of several fungi and isolated enzymes [14]. Baker's yeast was used to reduce several fluorinated compounds with rather high enantioselectivity and alcohol dehydrogenase from Leifsonia sp.…”

Section: Resultsmentioning

confidence: 99%

Bioreduction of fluoroacetophenone derivatives by endophytic fungi isolated from the marine red alga Bostrychia radicans

Mouad¹,

Oliveira²,

Debonsi³

et al. 2016

Biocatalysis

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Four endophytic fungi isolated from the marine red alga Bostrychia radicans identified as Botryosphaeria sp. CBMAI 1197, Eutypella sp. CBMAI 1196, Hidropisphaera sp. CBMAI 1194 and Xylaria sp. CBMAI 1195 catalyzed the asymmetric bioreduction of fluoroacetophenone derivatives 1-3 to the corresponding fluorophenylalcohols 1a-3a. In the reduction reactions of 2,2,2-trifluoro-1-phenylethanone 1, all the marine fungi produced exclusively the (S)-2,2,2-trifluoro- 1-phenylethanol 1a with > 99% ee. The fungus Botryosphaeria sp. CBMAI 1197 exhibited the best enzymatic potential, leading to the highest conversion values (up to > 99%). The biocatalyst Botryosphaeria sp. CBMAI 1197 also presented active enzymes in reactions with the substrates 1-(2-(trifluoromethyl)phenyl) ethanone (2) and 1-(2,4,5-trifluorophenyl)ethanone (3), producing the respective chiral alcohols S-2a and R-3a with > 99% ee. Additionally, the fungus Hidropisphaera sp. CBMAI 1194 yielded 100% of conversion of the ketone 3 to the corresponding S-alcohol 3a, with 53% ee.

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Section: Resultsmentioning

confidence: 99%

Bioreduction of fluoroacetophenone derivatives by endophytic fungi isolated from the marine red alga Bostrychia radicans

Mouad¹,

Oliveira²,

Debonsi³

et al. 2016

Biocatalysis

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“…These findings indicate that acetophenone was converted to phenyl acetate through Baeyer-Villiger oxidation [38] (Fig. 6), which occurs frequently during biotransformations [35][36][37][38][39][40][41][42][43][44]. The reaction is as shown in Fig.…”

Section: Time Course Of Biotransformation Of Acetophenone By C Acutatummentioning

confidence: 98%

“…In contrast, 1-phenylethanol did not detectably react. Although numerous reports have used various biocatalysts to synthesize acetophenone, none has used B. cinerea as the biocatalyst [33][34][35][36][37][38][39][40][41][42].…”

Section: Biotransformation Of Acetophenone and (Rac)-1-phenylethanol mentioning

confidence: 99%

Biotransformation of acetophenone to 1-phenylethanol by fungi

Nagaki

Sato

Tanabe

et al. 2016

Trans. Mat. Res. Soc. Japan

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The fungi Botrytis cinerea and Colletotrichum acutatum were used to convert acetophenone to 1-phenylethanol. B. cinerea produced a 98.5% yield of 1-phenylethanol with an enantiomeric excess of 93.8%. Conversely, addition of 1-phenylethanol did not change the reaction rate or product composition. In contrast, the reaction catalyzed by C. acutatum was markedly slower, commencing only after an approximately three-day delay. The concentration of substrate decreased gradually over approximately 14 days, coinciding with increased production of 1-phenylethanol. Phenol was produced after 18 days, and the final yields of 1-phenylethanol and phenol were 38.1% and 61.5%, respectively.

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“…Plants are good choices in the removal of organics in environmental remediation (Macek et al, 2000) and as biocatalysts in asymmetric reduction (Matsuda et al, 2009 (Abhilash et al, 2009;Haritash and Kaushik, 2009), whereas they have not yet been explored in NPAHs reduction. Compared with whole-plant system, plant cell extracts offer experimental advantages in plant biodegradation capabilities, toxicity tolerance, and shorter culture periods (Doran, 2009).…”

Section: Introductionmentioning

confidence: 99%