Kinetic Resolution of Racemic -Methyl--propiothio
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- 作者：Bum-Yeol Hwang ; Hee Bong Lee ; Young Gyu Kim ; and Byung-Gee Kim
- 刊名：Biotechnology Progress
- 出版年：2000
- 出版时间：December 2000
- 年：2000
- 卷：16
- 期：6
- 页码：973 - 978
- 全文大小：65K
- 年卷期：v.16,no.6(December 2000)
- ISSN：1520-6033
文摘
Kinetic resolution of racemic 
-methyl-
-propiothiolactone (rac-MPTL) using lipasesin organic solvent was studied. The lipase from Pseudomonas cepacia (PCL) showedthe highest (S)-enantioselectivity (E > 100), and cyclohexane containing 1% (v/v) bufferwas identified as the best reaction medium for maintaining high enantioselectivityas well as high reaction rate. While the substrate inhibition was not observed up to300 mM rac-MPTL, severe product inhibition was observed even at 50 mM racemic3-mercapto--methyl propionic acid (rac-MMPA), which made the use of high substrateconcentration difficult. To overcome the product inhibition, the products, (R)-MMPA,were neutralized by addition of a dilute basic solution. Although the resolution reactionproceeded further by the base titration, the enantioselectivity of the reaction decreasedas a result of nonenantioselective hydrolysis of rac-MPTL in the basic solution. Underthese conditions, 200 mM rac-MPTL was successfully resolved to above 95% eeS with53% conversion.
-methyl--propiothiolactone (rac-MPTL) using lipasesin organic solvent was studied. The lipase from Pseudomonas cepacia (PCL) showedthe highest (S)-enantioselectivity (E > 100), and cyclohexane containing 1% (v/v) bufferwas identified as the best reaction medium for maintaining high enantioselectivityas well as high reaction rate. While the substrate inhibition was not observed up to300 mM rac-MPTL, severe product inhibition was observed even at 50 mM racemic3-mercapto--methyl propionic acid (rac-MMPA), which made the use of high substrateconcentration difficult. To overcome the product inhibition, the products, (R)-MMPA,were neutralized by addition of a dilute basic solution. Although the resolution reactionproceeded further by the base titration, the enantioselectivity of the reaction decreasedas a result of nonenantioselective hydrolysis of rac-MPTL in the basic solution. Underthese conditions, 200 mM rac-MPTL was successfully resolved to above 95% eeS with53% conversion.