Effect of organic solvents and ionic liquids on resolution of 2‐epoxyhexane by whole cells of Rhodotorula glutinis in a two‐liquid phase system. Issue 4 (4th July 2013)

• Record Type: Journal Article
• Authors: Matsumoto, Michiaki; Sugimoto, Takashi; Ishiguro, Yudai; Yamaguchi, Hiroyuki; Kondo, Kazuo
• Is Part Of: Journal of chemical technology & biotechnology. Volume 89:Issue 4(2014:Apr.)
• Page Start: 522
• Page End: 527
• Publication Date: 2013-07-04
• Subjects: Biotechnology -- Periodicals; Chemistry, Technical -- Periodicals; Chemical engineering -- Periodicals; Industries -- Environmental aspects -- Periodicals; 660
• DOI: 10.1002/jctb.4148
• Languages: English
• ISSNs: 0268-2575

Abstract

<abstract abstract-type="main" id="jctb4148-abs-0001"> <title>Abstract</title> <sec id="jctb4148-sec-0001" sec-type="section"> <title>BACKGROUND</title> <p id="jctb4148-para-0001"> <bold>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 <italic>rac</italic>‐epoxide in a biphasic system using whole cell catalysts is one of the promising methods to obtain enantiopure compounds</bold>.</p> </sec> <sec id="jctb4148-sec-0002" sec-type="section"> <title>RESULTS</title> <p id="jctb4148-para-0002"> <bold>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 (<italic>R</italic>)‐enantiomer, <italic>r</italic><sub>R0</sub> and enantiomeric ratio, <italic>E</italic> was examined. In the case of using hydrophobic hydrocarbons, <italic>r</italic><sub>R0</sub> increased with the hydrophobicity of hydrocarbon (log <italic>P</italic><sub>O/W</sub>), and a linear correlation was observed between <italic>r</italic><sub>R0</sub> and log <italic>P</italic><sub>O/W</sub>. On the other hand, there were no correlations between <italic>r</italic><sub>R0</sub> and log <italic>P</italic><sub>O/W</sub> of ionic liquids. Moreover, effects on <italic>E</italic> were small in both solvents. However, the addition of 1‐heptanol to dodecane was very effective at increasing <italic>E</italic> value. The kinetic data correlated well with the reaction kinetic model, considering the distribution between two liquid phases and competitive product inhibition</bold>.</p> </sec> <sec id="jctb4148-sec-0003" sec-type="section"> <title>CONCLUSION</title> <p id="jctb4148-para-0003"> <bold>The high enantiomeric ratio of (<italic>R</italic>)‐diol (<italic>E</italic>>100) without significant decrease in the reactivity was accomplished by adding 1‐heptanol in minute amounts to dodecane. © 2013 Society of Chemical Industry</bold> </p> </sec> </abstract>