Optimization for two-step biochemical kinetic resolution of enantiomers

Biocatalysis and Biotransformation

Volumn 23, Issue 2, 2005, Pages 97-101

  Zhu, Shengdong ^a   Wu, Yuanxin ^b   Yu, Ziniu ^b  

^a WUHAN INSTITUTE OF TECHNOLOGY   (China)

^b HUAZHONG AGRICULTURAL UNIVERSITY   (China)

Author keywords

Biochemical kinetic resolution; Ketoprofen; Optimization

Indexed keywords

ESTERIFICATION; ESTERS; HYDROLYSIS; OPTIMIZATION;

BIOCHEMICAL KINETIC RESOLUTION; ENANTIOMERS; ENANTIOSELECTIVE HYDROLYSIS; KETOPROFEN;

POLYMERS;

KETOPROFEN;

ARTICLE; BIOCHEMISTRY; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MATHEMATICAL COMPUTING; PROCESS OPTIMIZATION; RACEMIC MIXTURE;

EID: 21844478497     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.1080/10242420500090177     Document Type: Article

References (16)

1. Allenmark S, Ohlsson A. 1992. Enantioselectivity of lipased-catalyzed hydrolysis of some 2-chloroethyl 2-arylpropanoates studied by chiral reversed-phase liquid chromatography. Chirality 4:98-102.
2. Antona ND, Lombardi P, Nicolosi G, Salvo G. 2002. Large scale preparation of enantiopure ketoprofen by biocatalysed kinetic resolution. Process Biochem 38:373-7.
3. Chamorro S, Montero JMS, Alcantara AR, Sinisterra JV. 1998. Treatment of Candida rugosa lipase with short chain polar organic solvents enhances its hydrolytic and synthetic activities. Biotechnol Lett 20:499-505.
4. Chen CS, Fujimoto Y, Girdaukas G, Sih CJ. 1982. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 104:7294-9.
5. Chen CS, Liu YC. 1991. Amplification of enantioselectivity in biocatalyzed kinetic resolution of racemic alcohols. J Org Chem 56:1966-8.
6. Chen CS, Wu SH, Girdaukas G, Charles JS. 1987. Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biophasic systems. J Am Chem Soc 109:2812-7.
7. Evans, CT, McCauge, R, Taylor, SJC and Carganico, G. 1993. Arylalkanoic acid resolution. WO 93/04190.
8. Guo ZW. 1993. Novel plots of data from combined multi-step enzymatic resolutions of enantiomers. J Org Chem 58:5748-52.
9. Guo ZW, Sih CJ. 1989. Enantioselective inhibition: a strategy for improving the enantioselectivity of biocatalytic systems. J Am Chem Soc 111:6836-41.
10. Guo ZW, Wu SH, Chen CS, Girdaukas G, Sih CJ. 1990. Sequential biocatalytic kinetic resolution. J Am Chem Soc 112:4942-5.
11. Jimenez O, Bosch MP, Guerrero A. 1997. Lipase-catalyzed enantioselective synthesis of methyl (R)-and (S)-2-tetradecyloxirane carboxylate through sequential kinetic resolution. J Org Chem 62:3496-9.
12. Lalonde JJ, Govardhan C, Khalaf N, Martinez AG, Visuri K, Margolin AL. 1995. Cross-linked crystals of Candida rugosa lipase: highly efficient catalysts for resolution of chiral esters. J Am Chem Soc 117:6845-52.
13. Liu YY, Xu JH, Xu QG, Hu Y. 1999. Significant enhancement of lipase enantioselectivity toward S-ketoprofen ester at pH 2. Biotechnol Lett 21:143-6.
14. Scilimati A, Ngooi TK, Sih CJ. 1988. Biocatalytic resolution of (±)-hydroxyalkanoic esters. A strategy for enhancing the enantiomeric specificity of lipase-catalyzed ester hydrolysis. Tetrahedron Lett 29:4927-30.
15. Wu SH, Guo ZW, Sih CJ. 1990. Enhancing the enantioselectivity of Candida lipase catalyzed ester hydrolysis via noncovalent enzyme modification. J Am Chem Soc 112: 1990-5.
16. Xin JY, Li SB, Chen XH, Wang LL, Xu Y. 2000. Improvement of enantioselectivity of lipase-catalyzed naproxen ester hydrolysis in organic solvent. Enzyme Microb Technol 26: 137-41.