Table 2.
Effect of organic co-solvent on the preparation of LSC and LSC-catalyzed kinetic resolution of (RS)-1-PE
| Co-solvent | Log P | LSC yield (g)a | Protein recovery (%)a | Conversion (% at 2 h)a | eep (% at 2 h) | E |
|---|---|---|---|---|---|---|
| Water | 0.108 ± 0.003 | 9.7 ± 0.3 | 32.4 ± 1.6 | > 99 | > 200 | |
| DMSO | − 1.3 | 0.104 ± 0.005 | 8.4 ± 0.4 | 2.0 ± 0 | > 99 | > 200 |
| DMF | − 1 | 0.096 ± 0.006 | 10.9 ± 0.7 | 20.6 ± 1.6 | > 99 | > 200 |
| Acetonitrile | − 0.33 | 0.102 ± 0.004 | 9.0 ± 0.4 | 5.0 ± 0.3 | > 99 | > 200 |
| Ethanol | − 0.24 | 0.130 ± 0.013 | 11.8 ± 1.3 | 6.3 ± 0.5 | > 99 | > 200 |
| Acetone | − 0.23 | 0.102 ± 0.008 | 9.5 ± 0.8 | 10.7 ± 0.7 | > 99 | > 200 |
| THF | 0.49 | 0.108 ± 0.004 | 9.3 ± 0.5 | 46.8 ± 2.3 | > 99 | > 200 |
| tert-Butanol | 0.6 | 0.109 ± 0.014 | 10.5 ± 1.2 | 11.9 ± 1.0 | > 99 | > 200 |
Reaction conditions: 1 mmol (RS)-1-PE, 1 mmol vinyl acetate, and 100 mg LSC in 10 mL MTBE, reaction temperature 30 °C, shaking speed 200 rpm, reaction time 2 h
DMSO dimethyl sulfoxide, DMF N,N-dimethyl formamide, THF tetrahydrofuran
aMean value ± standard deviation for at least three determinations