Enantioselective transesterification using lipase-displaying yeast whole-cell biocatalyst.
An enantioselective transesterification in non-aqueous organic solvent was developed by utilizing a lipase-displaying yeast whole cell biocatalyst constructed in our previous study. As a model reaction, optical resolution of (RS)-1-phenylethanol, which serves as one of chiral building blocks, was carried out by enantioselective transesterification with vinyl acetate. Recombinant Rhizopus oryzae lipase displayed on the yeast cell surface retained its activity in hexane, heptane, cyclohexane and octane. The effective amount of whole-cell biocatalyst in the reaction mixture was 10 mg/ml solvent. In a reaction mixture incubated for 36 h with molecular sieves 4A, the concentration of (R)-1-phenylethyl acetate reached 39.8 mM (97.3% yield) with high enantiomeric excess (93.3%ee). In contrast, a reaction mixture incubated without molecular sieves 4A produced little (R)- and (S)-1-phenylethyl acetate. The results obtained in this study demonstrate the applicability of the lipase-displaying yeast whole cell biocatalyst to bioconversion processes in non-aqueous organic solvents.
Matsumoto
T
T
Division of Molecular Science, Graduate School of Science and Technology, Kobe University, 1-1 Rokkodaicho, Nada-ku, 657-8501 Kobe, Japan.
Ito
M
M
Fukuda
H
H
Kondo
A
A
D001592:Benzyl Alcohols / Q000378:metabolism; D001711:Biotransformation; D003001:Cloning, Molecular; D003510:Cyclohexanes / Q000378:metabolism; D004951:Esterification; D005800:Genes, Fungal; D006536:Heptanes; D006586:Hexanes / Q000378:metabolism; D008049:Lipase / Q000235:genetics* / Q000378:metabolism*; D008565:Membrane Proteins / Q000235:genetics* / Q000378:metabolism*; D009795:Octanes / Q000378:metabolism; D011994:Recombinant Proteins / Q000235:genetics / Q000378:metabolism; D012233:Rhizopus / Q000201:enzymology*; D012441:Saccharomyces cerevisiae / Q000235:genetics / Q000378:metabolism; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000378:metabolism
D001592:Benzyl Alcohols; D003510:Cyclohexanes; D006536:Heptanes; D006586:Hexanes; D008565:Membrane Proteins; D009795:Octanes; D011994:Recombinant Proteins; D014753:Vinyl Compounds; C002017:methylphenyl carbinol; D008049:Lipase; C011566:vinyl acetate; C026728:octane