Regioselective enzymatic acylation and deacetylation of secoiridoid glucosides.
Candida antarctica lipase (CAL) catalyses the regioselective cinnamoylation and benzoylation of the aglycone moiety of 10-hydroxyoleoside dimethyl ester a secoiridoid glucoside. This enzyme catalyses as well regioselective deacetylation of the aglycone moiety of 10,2',3',4',6'-pentaacetoxyoleoside dimethyl ester. Further action of the enzyme results in deacetylation at C-6' and C-4' of the glucoside moiety.
Pérez
José Andrés
JA
Instituto Universitario de Bioorgánica, Universidad de La Laguna, Tenerife, Canary Island, Spain. japerez@ull.es
Trujillo
Juan Manuel
JM
López
Hermelo
H
Aragón
Zulma
Z
Boluda
Carlos
C
D000107:Acetylation; D000215:Acylation; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D039823:Iridoids / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D008968:Molecular Conformation; D012015:Reference Standards; D013237:Stereoisomerism
D039823:Iridoids; D008049:Lipase