Kinetic resolution of racemic 1-phenyl 1-propanol by lipase catalyzed enantioselective esterification reaction.
In this study, resolution of (R,S)-1-phenyl 1-propanol by lipase-catalyzed enantioselective esterification was achieved. To investigate the effect of lipase type on enantiomeric excess, three different lipases were used. Novozym 435 exhibited the highest enantioselectivity for resolution of (R,S)-1-phenyl 1-propanol. The effects of carbon length of fatty acids from C12 to C16, which were used as acyl donor, organic solvents with Log P values from 0.5 to 4.5, acyl donor/alcohol molar ratio (1:1, 3:2, 2:1, 3:1), amount of added molecular sieves (0-133.2 kg/m(3)), and temperature (10-60° C) on the enantioselectivity were investigated. The best reaction conditions were comprised of using toluene (Log P= 2.5) as solvent, lauric acid (12C) as acyl donor, 133.2 kg/m(3) molecular sieves at 50° C and acyl donor/alcohol molar ratio as 1:1. Under these conditions, the enantiomeric excess of S enantiomer ee (S) was obtained as 95% for a reaction time of 2.5 hours.
Karadeniz
Fatma
F
Biotechnology Institute, Ankara University, Tandogan, Ankara, Turkey.
Bayraktar
Emine
E
Mehmetoglu
Ulkü
U
D055162:Biocatalysis; D002175:Candida / Q000201:enzymology; D004951:Esterification; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D020005:Propanols / Q000737:chemistry* / Q000378:metabolism*; D011549:Pseudomonas / Q000201:enzymology; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature
D020005:Propanols; D012997:Solvents; C439395:1-phenylpropanol; D008049:Lipase