Effects of Solvent and Substrate on Enantioselectivity in Pseudomonas cepacia Lipase Catalyzed Transesterification between Tributyrylglycerol and 2-Alkanol in Organic Solvent

Kinetic Resolution of Optically Pure 3-Alkanol by Pseudomonas cepacia Lipase-Catalyzed Transesterification with Vinyl Acetate in Organic Solvent

“…Table 4 shows that 1,2-dichloroethane, acetonitrile and acetone gave higher E than the other solvents. A similsr tendency has been reported in PCL-catalyzed transesterification between TB and secondary alcohol (18)(19)(20)(21) and also in the reaction between VA and 2-alkanol (14). Thus, we selected 1,2-dichloroethane and acetonitrile as the reaction solvents and also used hexane as a standard solvent in the following studies.…”

“…It has been reported that E is affected by a combination of the structures of solvent and substrate and the solvent hydrophobicity (log P) in PCL-catalyzed transesterification with tributyrylglycerol (TB) (19)(20)(21). We therefore screened more than a dozen solvents for PCLcatalyzed transesterification between VA and (RS)-83-OH at 30 .…”

Kinetic Resolution of Enantiomers in Racemic and Enantiomerically Enriched 2-Alkanols by <i>Pseudomonas cepacia</i> Lipase Catalyzed Transesterification with Isopropenyl Acetate in Organic Solvent

“…The E value roughly decreased with log P except the bulky solvents such as dioxane, cyclohehane and carbon tetrachloride. In this paper, the bulky solvents mean those having a large cross plane perpendicular to the major axis of solvent molecule (29). In those solvents, the E values were smaller than those expected from log P. A similar tendency was observed in PCL catalyzed transesterification with TB (28,29) and also with VA (17,19).…”

“…If E calculated by Eq. (2) for the reversible reaction, it essentially decreases as c increases (11)(12)(13)(14). However, it has been reported that E can be determined by Eq.…”

“…However, it has been reported that E can be determined by Eq. (2) in the range of c where the reverse reaction is negligible even though the reaction is reversible (12)(13)(14).…”