Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones

被引:16
作者
Sahin, Engin [1 ]
机构
[1] Bayburt Univ, Dept Food Engn, Fac Engn, TR-69000 Bayburt, Turkey
关键词
Bio reduction: asymmetric reduction; whole yeast cells; Debaryomyces hansenii; bio transformations; TRANSFER HYDROGENATION; KETONES; HYPERPARATHYROIDISM; CALCIMIMETICS; BIOREDUCTION; CATALYSTS; ISOLATE; YEAST;
D O I
10.1080/10242422.2017.1348500
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Chiral secondary alcohols are convenient mediator for the synthesis of biologically active compounds and natural products. In this study fifteen yeast strains belonging to three food originated yeast species Debaryomyces hansenii, Saccharomyces cerevisiae and Hanseniaspora guilliermondii were tested for their capability for the asymmetric reduction of acetophenone to 1-phenylethanol as biocatalyst microorganisms. Of these strains, Debaryomyces hansenii P1 strain showed an effective asymmetric reduction ability. Under optimized conditions, substituted acetophenones were converted to the corresponding optically active secondary alcohols in up to 99% enantiomeric excess and at high conversion rates. This is the first report on the enantioselective reduction of acetophenone by D. hansenii P1 from pastirma, a fermented Turkish meat product. The preparative scale asymmetric bio reduction of 3-methoxy acetophenone 1g by D. hansenii P1 gave (R)-1-(3-methoxyphenyl) ethanol 2g 82% yield, and >99% enantiomeric excess. Compound 2g can be used for the synthesis of (+)-NPS-R-568 [3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenly) ethyl] propan-1-amine] which have a great potential for the treatment of primary and secondary hyper-parathyroidism. In addition, D. hansenii P1 successfully reduced acetophenone derivatives. This study showed that this yeast can be used industrially to produce enantiomerically pure chiral secondary alcohols, which can be easily converted to different functional groups.
引用
收藏
页码:363 / 371
页数:9
相关论文
共 33 条
  • [1] LACTOBACILLUS-KEFIR ALCOHOL-DEHYDROGENASE - A USEFUL CATALYST FOR SYNTHESIS
    BRADSHAW, CW
    HUMMEL, W
    WONG, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1532 - 1536
  • [2] Cloning, Expression, and Characterization of a Novel (S)-Specific Alcohol Dehydrogenase from Lactobacillus kefir
    Chen, Qilei
    Hu, Youjia
    Zhao, Wenjie
    Zhu, Chunbao
    Zhu, Baoquan
    [J]. APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 2010, 160 (01) : 19 - 29
  • [3] Calcimimetics: therapeutic potential in hyperparathyroidism
    Cohen, A
    Silverberg, SJ
    [J]. CURRENT OPINION IN PHARMACOLOGY, 2002, 2 (06) : 734 - 739
  • [4] Deracernization of aryl ethanols and reduction of acetophenones by whole fungal cells of Aspergillus terreus CCT 4083, A-terreus CCT 3320 and Rhizopus oryzae CCT 4964
    Comasseto, JV
    Andrade, LH
    Omori, AT
    Assis, LF
    Porto, ALM
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 29 (1-6) : 55 - 61
  • [5] Dehydrogenases/Reductases for the Synthesis of Chiral Pharmaceutical Intermediates
    Huang, Yan
    Liu, Nan
    Wu, Xuri
    Chen, Yijun
    [J]. CURRENT ORGANIC CHEMISTRY, 2010, 14 (14) : 1447 - 1460
  • [6] Calcimimetics and the treatment of primary and secondary hyperparathyroidism
    Joy, MS
    Kshirsagar, AV
    Franceschini, N
    [J]. ANNALS OF PHARMACOTHERAPY, 2004, 38 (11) : 1871 - 1880
  • [7] Enzymatic production of ethyl (R)-4-chloro-3-hydroxybutanoate:: asymmetric reduction of ethyl 4-chloro-3-oxobutanoate by an Escherichia coli transformant expressing the aldehyde reductase gene from yeast
    Kataoka, M
    Rohani, LPS
    Yamamoto, K
    Wada, M
    Kawabata, H
    Kita, K
    Yanase, H
    Shimizu, S
    [J]. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1997, 48 (06) : 699 - 703
  • [8] Asymmetric reduction of acetophenone analogues by Alternaria alternata using ram horn peptone
    Kurbanoglu, Esabi B.
    Zilbeyaz, Kani
    Kurbanoglu, Namudar I.
    Kilic, Hamdullah
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (19) : 2332 - 2335
  • [9] Efficient Synthesis of (S)-1-(2-chlorophenyl)ethanol in the Submerged Culture of Alternaria alternata Isolate
    Kurbanoglu, Esabi B.
    Taskin, Mesut
    Zilbeyaz, Kani
    Hasenekoglu, Ismet
    [J]. CHINESE JOURNAL OF CATALYSIS, 2009, 30 (04) : 370 - 374
  • [10] Direct Catalytic Synthesis of Unprotected 2-Amino-1-Phenylethanols from Alkenes by Using Iron(II) Phthalocyanine
    Legnani, Luca
    Morandi, Bill
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (06) : 2248 - 2251