Optimisation of the enantioselective biocatalytic hydrolysis of naproxen ethyl ester using ChiroCLEC-CR

Enzyme and Microbial Technology

Volumn 34, Issue 3-4, 2004, Pages 283-291

  Brady, Dean ^a   Steenkamp, Lucia ^a   Skein, Etienne ^a   Chaplin, Jennifer A ^a   Reddy, Shavani ^a  

^a DSI CSIR Nanotechnology Innovation Centre   (South Africa)

Author keywords

Candida rugosa lipase; ChiroCLEC CR; Enantioselectivity; Hydrolysis; Lipase; Naproxen ester; S Naproxen

Indexed keywords

BIOCATALYSTS; CATALYSIS; ENZYMES; HYDROLYSIS; OPTIMIZATION; PH EFFECTS; REACTION KINETICS; THERMAL EFFECTS;

ENANTIOSELECTIVITY;

ESTERS;

BUFFER; ESTER DERIVATIVE; MACROGOL 10000; NAPROXEN; RACEMASE; SOLVENT; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); ENANTIOSELECTIVITY; ENZYME SUBSTRATE; HYDROLYSIS; KINETICS; MICHAEL ADDITION; PH; REACTION TIME;

CANDIDA RUGOSA;

EID: 0442276344     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2003.11.002     Document Type: Article

References (14)

1. Hernaiz M.J., Sanchez-Montero J.M., Sinisterra J.V. Comparison of the activity of commercial and semipurified lipase of Candida cylindracea in the hydrolysis of ester of (R,S)-2-aryl propionic acid. Tetrahedron. 50:1994;10749-10760.
2. Wu S.H., Guo Z.W., Sih C.J. Enhancing the enantioselectivity of Candida lipase catalysed hydrolysis via noncovalent enzyme modification. J. Am. Chem. Soc. 112:1990;1990-1995.
3. Kazlauskas R.J., Weissfloch A.N.E., Rappaport A.T., Cuccia L.A. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa. J. Org. Chem. 56:1991;2656-2665.
4. Lalonde J.J., Govardhan C., Khalaf N., Martinez A.G., Visuri K., Margolin A.L. Cross-linked crystals of Candida rugosa lipase: highly efficient catalysts for the resolution of chiral esters. J. Am. Chem. Soc. 117:1995;6845-6852.
5. Chibata J, editor. Immobilised enzymes. Tokyo, New York: Kodansho-Halsted Press; 1978.
6. ChiroCLEC-CR information booklet. Version 2.0 September 20, 1995. Published by Altus Biologics Inc., Cambridge, USA.
7. Roszkowski A.P., Rooks W.H., Tomolonis A.J., Miller L.M. Antiinflammatory and analgesic properties of d-2-(methoxy-2′-naphtyl)- propionic acid (naproxen). J. Pharmacol. Exp. Ther. 179:1971;114.
8. Battistel E., Bianchi D., Cesti P., Pina C. Enzymatic resolution of (S)-(+)-naproxen in a continuous reactor. Biotechnol. Bioeng. 38:1991;659-664.
9. Steenkamp L.H., Brady D. Screening of commercial enzymes for the enantioselective hydrolysis of (R,S)-naproxen ester. Enzyme Microbiol. Technol. 32(3/4):2003;472-477.
10. Ghazali H.M., Lai C.S. Hydrolytic activity of Candida rugosa lipase entrapped in aerosol-OT/isooctane reversed micelles: effect of temperature, pH, ionic strength, substrate concentrations and cations. Asia-Pacific J. Mol. Biol. Biotechnol. 4:1996;67-73.
11. Zacchigna M., di Luca G., Lassiani L., Varnavas A., Boccu E. Properties of methoxy(polyethylene glycol)-lipase from Candida rugosa in organic solvents. Farmaco. 53:1998;758-763.
12. Hacking M.A.P.J., van Rantwijk F., Sheldon R.A. Lipase catalysed acylation of hydroxylamine and hydrazine derivatives. J. Mol. Catal. B Enzymatic. 11(4/6):2001;315-321.
13. Xin J.Y., Li S.B., Chui J.R., Xia C.G. Dynamic enzymatic resolution of naproxen methyl ester in a membrane bioreactor. J. Chem. Technol. Biotechnol. 6:2001;579-585.
14. Lee E.G., Won H.S., Chung B.H. Enantioselective hydrolysis of racemic naproxen methyl ester by 2-step acetone-treated Candida rugosa lipase. Proc. Biochem. 37(3):2001;293-298.