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Lipase-catalyzed enantioselective hydrolysis of methyl 2-fluoro-2-arylpropionates in water-saturated isooctane |
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| Authors: | Pei-Yun Wang Teh-Liang Chen Shau-Wei Tsai Antonio Cipiciani Francesca Bellezza Renzo Ruzziconi |
| Institution: | aDepartment of Chemical Engineering, National Cheng Kung University, Tainan 70101, Taiwan bInstitute of Biochemical and Biomedical Engineering, Chang Gung University, 259 Wen-Hwa 1st Road, Kwei-Shan Tao-Yuan 33302, Taiwan cCentro di Eccellenza Materiali Innovativi Nanostrutturati, Università di Perugia, via Elce di Sotto 8, 06123 Perugia, Italy dLaboratorio composti fluororganici, Dipartimento di Chimica, Università di Perugia, via Elce di Sotto 8, 06123 Perugia, Italy |
| Abstract: | Lipases from Candida rugosa, Candida antartica B and Carica papaya are employed as the biocatalyst for the hydrolytic resolution of methyl 2-fluoro-2-arylpropionates in water-saturated isooctane, in which excellent to good enantioselectivity without the formation of byproducts is obtained for the papaya lipase when using (R,S)-2-fluoronaproxen methyl ester (1) and methyl (R,S)-2-fluoro-2-(4-methoxyphenyl)propionate (2), but not methyl (R,S)-2-fluoro-2-(naphth-1-yl)propionate (3) as the substrates. The thermodynamic analysis indicates that the enantiomer discrimination for the papaya lipase is driven by the difference in activation enthalpy for compound 1, 2 or (R,S)-naproxen methyl ester (4). The kinetic analysis also demonstrates that in comparison with (S)-4, the insertion of the 2-fluorine moiety in (R)-1 has increased k2, but not Km, and consequently the lipase activity. |
| Keywords: | Lipases Enantioselective hydrolysis Methyl 2-fluoro-2-arylpropionates Naproxen methyl ester |
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