Enzymatic resolution of (R, S)-Naproxen in water-saturated ionic liquid

Biocatalysis and Biotransformation

Volumn 23, Issue 5, 2005, Pages 353-361

  Xin, Jia Ying ^a,b   Zhao, Yong Jie ^b   Zhao, Guan Li ^a   Zheng, Yan ^a   Ma, Xing Sheng ^a   Xia, Chun Gu ^b   Li, Shu Ben ^b  

^a HARBIN UNIVERSITY OF COMMERCE   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Enantioselectivity; Ionic liquid; Lipase; Naproxen; Repetitive batch reaction; Selective enzymatic hydrolysis

Indexed keywords

BIOREACTORS; CATALYSIS; ENZYME IMMOBILIZATION; HYDROLYSIS; SILICA;

ENANTIOSELECTIVITY; IONIC LIQUID; LIPASE; REPETITIVE BATCH REACTION; SELECTIVE ENZYMATIC HYDROLYSIS;

ENZYME KINETICS;

IONIC LIQUID; NAPROXEN; SILICON DIOXIDE; TRIACYLGLYCEROL LIPASE;

ARTICLE; BATCH REACTOR; CALCULATION; CONTROLLED STUDY; CULTURE MEDIUM; DISSOLUTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME IMMOBILIZATION; ENZYME MECHANISM; HYDROLYSIS;

EID: 30844465937     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420500292401     Document Type: Article

References (20)

1. Akita, H and Enoki, Y and Yamada, H. (1998) Enzymatic hydrolysis in organic solvents for kinetic resolution of water-insoluble α-acyloxy esters with immobilized lipases Chem Pharm Bull, 37, pp. 2876 - 2878.
2. Bastida, A and Sabuquillo, P and Armisen, P and Fernaandez-Lafuente, R and Huguet, J and Guisaan, JM. (1998) A single-step purification, immobilization, and hyperactivation of lipases via interfacial adsorption on strongly hydrophobic supports Biotechnol Bioeng, 50, pp. 486.
3. Battistel, E and Bianchi, D and Cesti, P and Pina, C. (1991) Enzymatic resolution of (S)-(+)-Naproxen in a continuous reactor Biotechnol Bioeng, 38, pp. 659 - 664.
4. Bradford, MM. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal Biochem, 72, pp. 248 - 254.
5. Cambou, B and Klibanov, AM. (1984) Comparison of different strategies for the lipase-catalyzed resolution of racemic acid and alcohols: asymmetric hydrolysis, esterification, and transesterification Biotechnol Bioeng, 26, pp. 1449 - 1454.
6. Caron, G and Kazlauskas, RJ. (1993) Sequential resolution of (2,3)-butanediol in organic solvent using lipase Tetrahedron Asymm, 4, pp. 1995 - 2000.
7. Chang, CS and Tsai, SW and Jimmy, K. (1999) Lipase-catalyzed dynamic resolution of Naproxen 2,2,2-trifluoroethyl thioester by hydrolysis in isooctane Biotechnol Bioeng, 64, pp. 120 - 126.
8. Chen, CS and Wu, SH and Girdauks, G and Sih, CJ. (1987) Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphase system J Am Chem Soc, 109, pp. 2812 - 2817.
9. Duan, G and Ching, CB and Lim, E and Ang, CH. (1997) Kinetic study of enantioselective esterification of ketoprofen with n-propanol catalysed by an lipase in an organic medium Biotechnol Lett, 19, pp. 1051 - 1055.
10. Erbeldinger, M and Mesiano, AJ and Russell, AJ. (2000) Enzymatic catalysis of formation of z-aspartame in ionic liquid - an alternative to enzymatic catalysis in organic solvents Biotechnol Prog, 16, pp. 1129 - 1131.
11. Halling, PJ. (1987) Biocatalysis in multi-phase reaction mixtures containing organic liquids Biotechnol Adv, 5, pp. 47 - 84.
12. Huddleston, JG and Willauer, HD and Swatloski, RP and Visser, AE and Rogers, RD. (1998) Room temperature ionic liquids as novel media for 'clean' liquid-liquid extraction Chem Comm, 16, pp. 1756 - 1766.
13. Hutt, AJ and Caldwell, J. (1984) The importance of stereochemistry in the clinical pharmacokinetics of the 2-arylpropionic acid non-steroidal anti-inflammatory drugs Clin Pharmacokinet, 9, pp. 371 - 373.
14. Kise, H and Tomiuchi, Y. (1991) Unusual solvent effect on protease activity and effective optical resolution of amino acids by hydrolytic reactions in organic solvents Biotechnol Lett, 13, pp. 317 - 322.
15. Park, S and Kazlauskas, RJ (2001) Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations J Organic Chem, 66, pp. 8395 - 8401.
16. Rakels, JLL and Straathof, AJJ and Heijnen, JJ. (1994) Improvement of enantioselective enzymatic ester hydrolysis in organic solvent Tetrahedron Asymm, 5, pp. 93 - 100.
17. Susheel, JN and Jitendra, RH and Manikrao, MS. (2003) Lipase-catalysed polyester synthesis in 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid Tetrahedron Lett, 44, pp. 1371 - 1373.
18. Tsai, SW and Liu, BY and Chang, CS. (1996) Enhancement of (S)-Naproxen ester productivity from racemic Naproxen by lipase in organic solvents J Chem Technol Biotechnol, 65, pp. 156 - 162.
19. Xin, JY and Li, SB and Xu, Y and Wang, LL. (2000) Enzymatic resolution of S-(+)-Naproxen in a trapped aqueous-organic solvent biphase continuous reactor Biotechnol Bioeng, 68, pp. 78 - 83.
20. Xin JY, Zhao YJ, Shi YG, Li SB. (2005) Lipase-catalyzed naproxen methyl ester hydrolysis in water-saturated ionic liquid: significantly enhanced enantioselectivity and stability World J Microbial Biotechnol 21 pp. 193 - 199.