| Titre : | Kinetic and thermodynamic investigation of lipase - catalyzed hydrolysis of (R,S) - 3 - phenylbutyl azolides (2012) |
| Auteurs : | Jin-Ru Chen, Auteur ; Chia-Ching Wu, Auteur ; Pei-Yun Wang, Auteur |
| Type de document : | Article : texte imprimé |
| Dans : | Industrial & engineering chemistry research (Vol. 51 N° 9, Mars 2012) |
| Article en page(s) : | pp. 3580-3586 |
| Note générale : | Chimie industrielle |
| Langues : | Anglais |
| Tags : | Hydrolysis Enzymatic catalysis Kinetics |
| Résumé : | Water-saturated cydohexane at 25 °C is selected as the best reaction condition for Novozym 435-catalyzed hydrolytic resolution of (R,S)-3-phenylbutyl 4-methylpyazolide (1). The kinetic constants and enantiomeric ratio of 36 are then estimated from the kinetic analysis and successfully employed for simulating the time-course conversions of both enantiomers. A feed-batch operation with water added during the reaction is proposed for converting the fast-reacting enantiomer of high concentrations to the product. A linear enthalpy-entropy compensation relationship of ―ΔΔS = ―38.84 + 3.29(―ΔΔH) with R2 = 0.98 for the lipase-catalyzed hydrolysis or alcoholysis of several (R,S)-azolides in anhydrous or water-saturated solvents is addressed. The resolution platform is further extended to (R,S)-3-(Boc-amino)-3-phenylpropionyl 4-methylpyrazolide (10), leading to improved enzyme activity and enantioselectivity if anhydrous methyl tert-butyl ether or isopropanyl ether is selected as the reaction medium. |
| ISSN : | 0888-5885 |
| En ligne : | http://cat.inist.fr/?aModele=afficheN&cpsidt=25595784 |
