J. Palomo, Rosa L. Segura, C. Mateo
Feb 21, 2005
Citations
1
Influential Citations
62
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract The efficient enzymatic synthesis of enantiopure 2,3-epoxypropanol (glycidol) has been achieved. The racemic glycidyl butyrate was successfully resolved by enzymatic hydrolysis using a strategy that combines different immobilization protocols and different experimental reaction conditions. A new enzyme (25 kDa lipase)—which is a lipase-like enzyme purified from the pancreatic porcine lipase (PPL) extract—immobilized on DEAE–Sepharose was selected as the optimal biocatalyst. The optimal results were obtained at pH 7, 25 °C and 10% dioxane using this biocatalyst and a very high enantioselectivity for the enzyme was displayed, obtaining both ( R )-(−)-glycidyl butyrate and ( R )-(+)-glycidol with enantiomeric excesses >99% ( E >100). The hydrolysis of ( R )-(−)-glycidyl butyrate produced pure ( S )-(−)-glycidol.