Highly efficient asymmetric reduction of arylpropionic aldehydes by Horse Liver Alcohol Dehydrogenase through dynamic kinetic resolution

被引:50
作者
Giacomini, Daria
Galletti, Paola
Quintavalla, Arianna
Gucciardo, Gabriele
Paradisi, Francesca
机构
[1] Univ Bologna, Dept Chem G Ciamician, Ahna Mater Mater Studiorum, I-40126 Bologna, Italy
[2] UCD, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland
关键词
D O I
10.1039/b712290j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective synthesis of (2S)-2-phenylpropanol and ( 2S)-2-(4-iso-butylphenyl) propanol ((S)-Ibuprofenol) has been achieved by means of Horse Liver Alcohol Dehydrogenase (HLADH) in buffered aqueous solution or buffered organic solvent mixtures; under the reaction conditions, a dynamic kinetic resolution (DKR) process was realized with good reaction yields and enantiomeric ratios.
引用
收藏
页码:4038 / 4040
页数:3
相关论文
共 50 条
  • [31] Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols
    Xie, Jian-Hua
    Zhou, Zhang-Tao
    Kong, Wei-Ling
    Zhou, Qi-Lin
    Journal of the American Chemical Society, 2007, 129 (07): : 1868 - 1869
  • [32] Kinetic and modelling studies of NAD(+) and poly(ethylene glycol)-bound NAD(+) in horse liver alcohol dehydrogenase
    Vanhommerig, SAM
    Sluyterman, LAAE
    Meijer, EM
    BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 1996, 1295 (02): : 125 - 138
  • [33] Effects of hydrostatic pressure on horse liver alcohol dehydrogenase (HLADH): A new way of analyzing kinetic study
    Trovaslet, M
    Legoy, MD
    Dallet-Choisy, S
    CELLULAR AND MOLECULAR BIOLOGY, 2004, 50 (04) : 353 - 359
  • [34] Catalytic asymmetric transfer hydrogenation/dynamic kinetic resolution: an efficient synthesis of florfenicol
    Wang, Xinlong
    Xu, Lingjun
    Yan, Lingjie
    Wang, Haifeng
    Han, Sheng
    Wu, Yan
    Chen, Fener
    TETRAHEDRON, 2016, 72 (14) : 1787 - 1793
  • [35] Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols
    Xie, Jian-Hua
    Zhou, Zhang-Tao
    Kong, Wei-Ling
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) : 1868 - +
  • [36] Mechanistic enzymology of liver alcohol dehydrogenase - Kinetic and stereochemical characterization of retinal oxidation and reduction
    Pocker, Y
    Li, H
    ENZYMOLOGY AND MOLECULAR BIOLOGY OF CARBONYL METABOLISM 6, 1997, 414 : 331 - 338
  • [37] Highly Efficient Kinetic Resolution of PHANOL by Chiral Phosphoric Acid Catalyzed Asymmetric Acylation
    Mori, Keiji
    Kishi, Hiroki
    Akiyama, Takahiko
    SYNTHESIS-STUTTGART, 2017, 49 (02): : 365 - 370
  • [38] Asymmetric hydrogenation of 2-arylated cycloalkanones through dynamic kinetic resolution
    Ohkuma, T
    Li, J
    Noyori, R
    SYNLETT, 2004, (08) : 1383 - 1386
  • [39] Asymmetric synthesis of silylated α-amino acid esters through dynamic kinetic resolution
    Chen, JX
    Tunge, JA
    Norton, JR
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) : 4366 - 4369
  • [40] INFLUENCE OF COENZYME STRUCTURE ON THE TRANSIENT-CHEMICAL INTERMEDIATE FORMED DURING HORSE-LIVER ALCOHOL-DEHYDROGENASE-CATALYZED REDUCTION OF AROMATIC-ALDEHYDES
    TORREILLES, J
    GUERIN, MC
    BIOCHIMICA ET BIOPHYSICA ACTA, 1986, 869 (03) : 265 - 274