Enantioselective aminolysis of an alpha-chloroester catalyzed by Candida cylindracea lipase encapsulated in sol-gel silica glass.
[reaction: see text] Lipase from Candida cylindracea (CcL) encapsulated in porous silica glass by a sol-gel method catalyzes enantioselective aminolysis of ethyl 2-chloropropionate. A silica matrix enhances the enzyme activity, i.e., improves the yield. The scope and limitations of the aminolysis reaction were investigated, and dynamic kinetic resolution of the ester was achieved. Encapsulated lipase remains active when used repeatedly. Encapsulation much improves the chiral discrimination by lipase and makes this enzyme even more useful in organic chemistry.
Badjić
J D
JD
Department of Chemistry, Iowa State University, Ames 50011-3111, USA.
Kadnikova
E N
EN
Kostić
N M
NM
D000814:Aniline Compounds / Q000737:chemistry; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism*; D008968:Molecular Conformation; D011422:Propionates / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry; D013379:Substrate Specificity
D000814:Aniline Compounds; D004952:Esters; D011422:Propionates; C013813:4-anisidine; D012822:Silicon Dioxide; D008049:Lipase