Application of selectively acylated glycosides for the alpha-galactosidase-catalyzed synthesis of disaccharides.
4-Nitrophenyl alpha-D-galactopyranosyl-(1-->3)-6-O-acetyl-alpha-D-galactopyranoside was prepared in a transglycosylation reaction catalyzed by alpha-D-galactosidase from Talaromyces flavus using 4-nitrophenyl alpha-D-galactopyranoside as a glycosyl donor and 4-nitrophenyl 6-O-acetyl-alpha-D-galactopyranoside as an acceptor. 4-Nitrophenyl 6-O-acetyl-alpha-D-galactopyranoside and 4-nitrophenyl 6-O-acetyl-beta-D-galactopyranoside were prepared in a regioselective enzymic transesterification in pyridine-acetone catalyzed by the lipase PS from Burkholderia cepacia. A series of water-miscible organic solvents (acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, 2-methoxyethanol, pyridine, 2-methylpropan-2-ol, tetrahydrofuran, propargyl alcohol) were used as co-solvents in this enzymic reaction. Their influence on the activity and stability of the alpha-galactosidase from T. flavus was established. 2-Methylpropan-2-ol and acetone (increasing the solubility of the modified substrate acceptors and displaying the minimum impairment of the activity and stability of the enzyme) were used as co-solvents in transglycosylation reactions.
Simerská
P
P
Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, 142 20 Prague, Czechia.
Kuzma
M
M
Pisvejcová
A
A
Weignerová
L
L
Macková
M
M
Riva
S
S
Kren
V
V
D016956:Burkholderia cepacia / Q000201:enzymology; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D004187:Disaccharides / Q000096:biosynthesis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009598:Nitrophenylgalactosides / Q000096:biosynthesis / Q000138:chemical synthesis*; D012997:Solvents; D032901:Talaromyces / Q000201:enzymology; D000519:alpha-Galactosidase / Q000737:chemistry* / Q000378:metabolism
D004187:Disaccharides; D012997:Solvents; D009598:Nitrophenylgalactosides; D000519:alpha-Galactosidase