期刊文献+

面包酵母催化溶剂相不对称还原合成(R)-2-羟基-4-苯基丁酸乙酯 被引量:5

Enantioselective Synthesis of Ethyl(R)-2-Hydroxy-4-Phenylbutyrate Mediated by Saccharomyces cerevisiae in Organic Solvents
在线阅读 下载PDF
导出
摘要 研究有机溶剂中面包酵母催化2-氧代-4-苯基丁酸乙酯(OPBE)不对称还原合成(R)-2-羟基-4-苯基丁酸乙酯((R)-HPBE),分别考察有机溶剂种类、初始水含量、初始底物浓度、缓冲液pH值和添加剂等因素对OPBE转化率(COPBE)、HPBE产率(YHPBE)及(R)-HPBE的光学纯度(ee%)的影响。实验结果表明,乙醚为适宜反应介质,适宜pH为中性;反应初始水含量和初始底物浓度分别以w(H2O)=30 g/Lc、(OPBE)=5 mmol/L为佳。添加α-氯代苯乙酮(-αPC)对酵母预处理2 h后,(R)-HPBE的ee从35.52%提高为82.25%,COPBE和YHPBE分别从75.29%和46.02%提高到98.51%和75.82%。 The asymmetric reduction of ethyl-2-oxo-4-phenylbutyrate (OPBE) catalyzed by bakers' yeast(Saccharomyces cerevisiae) in organic solvent to synthesize optically active ethyl-2-hydroxy-4-phenylbutyrate (HPBE) was investigated in detail. The conditions for asymmetric reduction were also studied. The reaction was run in aqueous diethyl ether at 30℃ for 24h under the catalysis of bakers' yeast, which preincubated for 2h in the presence of phenacyl chloride. As a result, both higher chemical yield(78.25%) and higher stereoselectivity(82.25% ee) were obtained at the optimum pH 7.0, dosage of water 30 g/L and substrate concentration 5 mmol/L, respectively.
出处 《食品与生物技术学报》 CAS CSCD 北大核心 2006年第2期66-69,73,共5页 Journal of Food Science and Biotechnology
基金 江苏省自然科学基金项目(BK2004019)
关键词 面包酵母 不对称还原 (R)-2-羟基-4-苯基丁酸乙酯 溶剂相 Saccharomyces cerevisiae asymmetric reduction chiral ethyl-2-hydroxy-4-phenylbutyrate organic phase
  • 相关文献

参考文献9

  • 1林文清,张晓梅,宓爱巧.(R)-2-羟基-4-苯基丁酸乙酯的合成[J].合成化学,2002,10(5):385-390. 被引量:9
  • 2Nakmura K, Matsuda T. Asymmetric reduction of ketones by the acetone powder of Geotrichum candidum [J]. J Org Chem, 1998, 63(24):8957-8966.
  • 3王智,董桓,曹淑桂.手性拆分反应中酶立体选择性的调控[J].自然科学进展,2003,13(2):126-131. 被引量:3
  • 4De Smet M J, Kingma J, Witholt B. The effect of toluene on the structure and permeability of the outer and cytoplasmic membrances of escherichia coli [J]. Biochim Biophys Acta, 1978, 506:64-80.
  • 5Colja Laane, Sjef Boeren, Kees Vos. Rules for optimization of biocatalysis in organic solvents [J]. Biotechnol Bioeng,1987, 30: 81-87.
  • 6Gorman L S, Dordick J S. Papain Kinetics in the presence of a water-miscible organic solvent[J]. Biotechnol Bioeng,1991, 375:967-972.
  • 7Nakamura K, Kondo S, Kawai Y. Asymmetric reduction of ketopantolactone by baker's yeast [J]. Tetrahedron:Asymmetry, 1993, 4:1253-1254.
  • 8Nakanura K, Kondo S, Nakajima N. Mechanistic study for stereochemical control of microbial reduction of α-Keto esters in an organic solvent [J]. Tetrahedron, 1995, 51: 687-694.
  • 9Dao H D, Kawai Y, Hida K, et al. Reduction of alkyl 2-Oxo-4-phenylbutyrate as precursors of angiotensin converting enzyme (ACE) inhibitors [J]. Bull Chem Soe Jpn, 1998, 71:425-432.

二级参考文献2

共引文献9

同被引文献52

引证文献5

二级引证文献6

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部