Lipase-catalyzed regioselective synthesis of steryl (6'-O-acyl)glucosides.
The regioselective acylation of cholesteryl beta-D-glucoside, at the C-6 of the glucose moiety, was achieved using microbial lipases in organic solvents. With palmitic acid as an acyl donor 81 or 63% conversions of cholesteryl glucoside to its 6'-O-palmitoyl derivative were obtained using Candida antarctica or Rhizomucor miehei enzymes, respectively. High yields (64-92%) were also obtained with fatty acids 6:0-22:0 and 16:1 (n-7). The synthesis of cholesteryl (6'-O-palmitoyl)glucoside was also achieved via transesterification, using mono-, di- and tri-palmitoylglycerols or methyl and ethyl palmitate as acyl sources. With R. miehei lipase transesterification between methyl palmitate (80 mM) and cholesteryl glucoside (1 mM) proceeded after 24 h with a nearly quantitative yield (97%).
Paczkowski
Cezary
C
Faculty of Biology, Department of Biochemistry, Warsaw University, Miecznikowa 1, 02-096, Warsaw, Poland.
Musial
Arkadiusz
A
Wlodkowski
Leszek
L
Kalinowska
Malgorzata
M
Wojciechowski
Zdzislaw A
ZA
D002384:Catalysis; D004789:Enzyme Activation; D004795:Enzyme Stability; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D005960:Glucosides / Q000737:chemistry*; D007536:Isomerism; D008049:Lipase / Q000737:chemistry*; D013379:Substrate Specificity
D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D005960:Glucosides; C093666:Lipozyme; C093667:Novozyme 435; D008049:Lipase