dc.contributor.author | El-Behairy, Mohammed Farrag | |
dc.contributor.author | Sundby, Eirik | |
dc.date.accessioned | 2020-06-05T10:11:12Z | |
dc.date.available | 2020-06-05T10:11:12Z | |
dc.date.created | 2016-12-22T14:57:30Z | |
dc.date.issued | 2016 | |
dc.identifier.citation | RSC Advances. 2016, 6 (101), 98730-98736. | en_US |
dc.identifier.issn | 2046-2069 | |
dc.identifier.uri | https://hdl.handle.net/11250/2656961 | |
dc.description.abstract | The antiepileptic eslicarbazepine (S-licarbazepine) has been prepared in one step from its racemic form RS-licarbazepine via lipase catalysed kinetic resolution. A novel stereoselective simultaneous HPLC separations of RS-licarbazepine (1) and its racemic esters RS-2–5 have been developed on Lux® cellulose-2 column using cyclohexane/ethanol 1/1 v/v as mobile phase. The developed enantioselective HPLC separations have been utilized for monitoring of lipase catalyzed kinetic resolution of RS-licarbazepine (1). Lipase catalysed trans-esterification and hydrolysis reactions have been performed. Four different esters (acetate (2), propionate (3), butyrate (4) and benzoate (5)) have been investigated for both trans-esterification and hydrolysis using ten lipases from versatile origins. The best enantioselectivity was shown by trans-esterification of RS-licarbazepine with vinyl benzoate in MtBE as solvent and lipase from Candida rugosa where the pharmacologically active enantiomer, S-(+)-licarbazepine, has been accomplished [E = 31, ee = 97%, yield 84%, α20D = +105, c 0.001 g mL−1, CH3OH]. Molecular docking attributed the high enantioselectivity of the transesterification when using Candida rugosa lipase to unfavorable ligand contacts between the S-enantiomer and phenylalanine 296. | en_US |
dc.language.iso | eng | en_US |
dc.publisher | Royal Society of Chemistry | en_US |
dc.title | One-step lipase-catalysed preparation of eslicarbazepine | en_US |
dc.type | Peer reviewed | en_US |
dc.type | Journal article | en_US |
dc.description.version | publishedVersion | en_US |
dc.source.pagenumber | 98730-98736 | en_US |
dc.source.volume | 6 | en_US |
dc.source.journal | RSC Advances | en_US |
dc.source.issue | 101 | en_US |
dc.identifier.doi | 10.1039/c6ra23915c | |
dc.identifier.cristin | 1416933 | |
dc.description.localcode | © The Royal Society of Chemistry 2016 DOI: 10.1039/c6ra23915c | en_US |
cristin.ispublished | true | |
cristin.fulltext | original | |
cristin.qualitycode | 1 | |