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Resolution of (RS)-proglumide using lipase from Candida cylindraceae

Biomedical Sciences Research Institute Computer Science Research Institute Environmental Sciences Research Institute Nanotechnology & Advanced Materials Research Institute

Muralidhar, RV, Chirumamilla, RR, Ramachandran, VN, Marchant, R and Singh - Nee Nigam, Poonam (2002) Resolution of (RS)-proglumide using lipase from Candida cylindraceae. BIOORGANIC and; MEDICINAL CHEMISTRY, 10 (5). pp. 1471-1475. [Journal article]

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Abstract

Proglumide is used in the treatment of neuropathic pain. It acts by inhibiting peptide cholecystokinin (CCK). Neural injury produces an elevation in plasma CCK. Proglumide has been also shown to augment the analgesic effect of sustained release morphine in neuropathic pain. Currently proglumide is administered as a racemic mixture. In the present study, an attempt is made to separate the racemic Mixture of the drug using lipase obtained from Candida cylindracea by stereoselective esterification. Enzymatic stereoselective esterification was carried out in organic solvents. The resolution was studied using a chromatographic column with a chiral support and mass spectrometry. The reaction conditions for stereoselective esterification including amount of substrate, amount of enzyme. alcohol, solvent and temperature were optimised during the present investigation. Butanol and hexanol were found to be suitable for formation of S and R esters. respectively. Hexane was the best solvent for esterification and the optimum temperature was found to be 30 degreesC. (C) 2002 Elsevier Science Ltd. All rights reserved.

Item Type:Journal article
Faculties and Schools:Faculty of Life and Health Sciences > School of Biomedical Sciences
Research Institutes and Groups:Biomedical Sciences Research Institute
Biomedical Sciences Research Institute > Infection and Immunity/Microbiology
ID Code:2732
Deposited By:Professor Roger Marchant
Deposited On:15 Dec 2009 20:40
Last Modified:04 Aug 2011 09:47

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