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

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

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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
Faculty of Life and Health Sciences > School of Biomedical Sciences
Research Institutes and Groups:Biomedical Sciences Research Institute
Biomedical Sciences Research Institute > Nutrition Innovation Centre for Food and Health (NICHE)
ID Code:5483
Deposited By: Dr Poonam Singh - Nee Nigam
Deposited On:21 Dec 2009 10:38
Last Modified:10 May 2017 14:53

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