One-step lipase-catalysed preparation of eslicarbazepine
| العنوان: | One-step lipase-catalysed preparation of eslicarbazepine |
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| المؤلفون: | Mohammed Farrag El-Behairy, Eirik Sundby |
| المصدر: | 98730-98736 RSC Advances |
| بيانات النشر: | Royal Society of Chemistry (RSC), 2016. |
| سنة النشر: | 2016 |
| مصطلحات موضوعية: | chemistry.chemical_classification, biology, 010405 organic chemistry, Chemistry, General Chemical Engineering, 010401 analytical chemistry, General Chemistry, Transesterification, 01 natural sciences, 0104 chemical sciences, Candida rugosa, Kinetic resolution, Hydrolysis, Propionate, biology.protein, Organic chemistry, Stereoselectivity, Lipase, Enantiomer |
| الوصف: | 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. © The Royal Society of Chemistry 2016 DOI: 10.1039/c6ra23915c |
| وصف الملف: | application/pdf |
| تدمد: | 2046-2069 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::bd6a66f4935d1a7de7a1d83ac0649f56Test https://doi.org/10.1039/c6ra23915cTest |
| حقوق: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....bd6a66f4935d1a7de7a1d83ac0649f56 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 20462069 |
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