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

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EN
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.
Wydawca

Czasopismo
Rocznik
Tom
1
Numer
1
Opis fizyczny
Daty
otrzymano
2015-11-11
zaakceptowano
2015-12-14
online
2016-01-21
Twórcy
  • Laboratório de Química Orgânica e
    Biocatálise, Instituto de Química de São Carlos, Universidade de
    São Paulo, Av. João Dagnone, 1100, Ed. Química Ambiental, J. Santa
    Angelina, 13563-120, São Carlos, São Paulo, Brazil
  • Laboratório de
    Química Orgânica do Ambiente Marinho, Faculdade de Ciências
    Farmacêuticas de Ribeirão Preto, Universidade de São Paulo,Via do
    Café s/n, 14040-903, Ribeirão Preto, São Paulo, Brazil
  • Laboratório de
    Química Orgânica do Ambiente Marinho, Faculdade de Ciências
    Farmacêuticas de Ribeirão Preto, Universidade de São Paulo,Via do
    Café s/n, 14040-903, Ribeirão Preto, São Paulo, Brazil
  • Laboratório de Química Orgânica e
    Biocatálise, Instituto de Química de São Carlos, Universidade de
    São Paulo, Av. João Dagnone, 1100, Ed. Química Ambiental, J. Santa
    Angelina, 13563-120, São Carlos, São Paulo, Brazil
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_1515_boca-2015-0011
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