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Effect of organic solvents and ionic liquids on resolution of 2‐epoxyhexane by whole cells of Rhodotorula glutinis in a two‐liquid phase system
Author(s) -
Matsumoto Michiaki,
Sugimoto Takashi,
Ishiguro Yudai,
Yamaguchi Hiroyuki,
Kondo Kazuo
Publication year - 2014
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.4148
Subject(s) - enantiopure drug , chemistry , kinetic resolution , ionic liquid , dodecane , epoxide , enantiomer , enantioselective synthesis , organic chemistry , heptanol , micelle , catalysis , biochemistry , intracellular , gap junction , aqueous solution
BACKGROUND Enantiopure epoxides and diols have attracted much attention as important building blocks for the production of flavorings, agrochemicals and pharmaceutical products. Enantioselective hydrolysis reaction of rac ‐epoxide in a biphasic system using whole cell catalysts is one of the promising methods to obtain enantiopure compounds . RESULTS The kinetic resolution of racemic 1,2‐epoxyhexane was carried out using whole cell biocatalyst in a hydrophobic solvent/buffer biphasic system and the effect of organic solvents and ionic liquids on the initial reaction rate of ( R )‐enantiomer, r R0 and enantiomeric ratio, E was examined. In the case of using hydrophobic hydrocarbons, r R0 increased with the hydrophobicity of hydrocarbon (log P O/W ), and a linear correlation was observed between r R0 and log P O/W . On the other hand, there were no correlations between r R0 and log P O/W of ionic liquids. Moreover, effects on E were small in both solvents. However, the addition of 1‐heptanol to dodecane was very effective at increasing E value. The kinetic data correlated well with the reaction kinetic model, considering the distribution between two liquid phases and competitive product inhibition . CONCLUSION The high enantiomeric ratio of ( R )‐diol ( E >100) without significant decrease in the reactivity was accomplished by adding 1‐heptanol in minute amounts to dodecane. © 2013 Society of Chemical Industry