Ionic liquid engineering for lipase - mediated optical resolution of secondary alcohols / Yoshikazu Abe in Industrial & engineering chemistry research, Vol. 51 N° 30 (Août 2012)  

Public ISBD [article]  inIndustrial & engineering chemistry research > Vol. 51 N° 30 (Août 2012) . - pp. 9952-9958 Titre : Ionic liquid engineering for lipase - mediated optical resolution of secondary alcohols : Design of ionic liquids applicable to ionic liquid coated - lipase catalyzed reaction Type de document : texte imprimé Auteurs : Yoshikazu Abe, Auteur ; Yusuke Yagi, Auteur ; Shuichi Hayase, Auteur Année de publication : 2012 Article en page(s) : pp. 9952-9958 Note générale : Industrial chemistry Langues : Anglais (eng) Mots-clés : Enzymatic catalysis Design Ionic liquid Résumé : A rational design of phosphonium ionic liquid for ionic liquid coated-lipase (IL1-PS)-catalyzed reaction has been investigated: very rapid transesterification of secondary alcohols was accomplished when IL1-PS was used as catalyst in tributyl((2-methoxyethoxy)methyl)phosphonium bis(trifluoromethanesulfonyl)amide ([P444MEM][NTf2]) or N-ethyl-N-((2-methoxyethoxy)methyl)-N-methylethanaminium bis(trifluoromethanesulfonyl)amide ([N221MEM[NTf2]) as solvent with excellent enantioselectivity. It was also revealed that ammonium ionic liquid influenced the lipase reactivity more strongly than phosphonium ionic liquids. Increased Kcat value was suggested to be the most important factor at work in IL1-PS in these ionic liquid solvents. The Kcat value of (S)-1-phenyethanol in [N44MEM][NTf2] was similar to that of i-Pr2O, and 1.6-fold acceleration was achieved for (R)-1-phenylethanol. On the other hand, the Km value for (R)-isomer in [N444MEM][NTf2] was slightly larger than the reaction in i-Pr2O, while it was significantly reduced for (S)-isomer. These results suggest that solvent provides a certain impact on the reactivity of the enzyme protein of IL1-PS. ISSN : 0888-5885 En ligne : http://cat.inist.fr/?aModele=afficheN&cpsidt=26201407 [article] Ionic liquid engineering for lipase - mediated optical resolution of secondary alcohols : Design of ionic liquids applicable to ionic liquid coated - lipase catalyzed reaction [texte imprimé] / Yoshikazu Abe, Auteur ; Yusuke Yagi, Auteur ; Shuichi Hayase, Auteur . - 2012 . - pp. 9952-9958. Industrial chemistry Langues : Anglais (eng) in Industrial & engineering chemistry research > Vol. 51 N° 30 (Août 2012) . - pp. 9952-9958 Mots-clés : Enzymatic catalysis Design Ionic liquid Résumé : A rational design of phosphonium ionic liquid for ionic liquid coated-lipase (IL1-PS)-catalyzed reaction has been investigated: very rapid transesterification of secondary alcohols was accomplished when IL1-PS was used as catalyst in tributyl((2-methoxyethoxy)methyl)phosphonium bis(trifluoromethanesulfonyl)amide ([P444MEM][NTf2]) or N-ethyl-N-((2-methoxyethoxy)methyl)-N-methylethanaminium bis(trifluoromethanesulfonyl)amide ([N221MEM[NTf2]) as solvent with excellent enantioselectivity. It was also revealed that ammonium ionic liquid influenced the lipase reactivity more strongly than phosphonium ionic liquids. Increased Kcat value was suggested to be the most important factor at work in IL1-PS in these ionic liquid solvents. The Kcat value of (S)-1-phenyethanol in [N44MEM][NTf2] was similar to that of i-Pr2O, and 1.6-fold acceleration was achieved for (R)-1-phenylethanol. On the other hand, the Km value for (R)-isomer in [N444MEM][NTf2] was slightly larger than the reaction in i-Pr2O, while it was significantly reduced for (S)-isomer. These results suggest that solvent provides a certain impact on the reactivity of the enzyme protein of IL1-PS. ISSN : 0888-5885 En ligne : http://cat.inist.fr/?aModele=afficheN&cpsidt=26201407

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