Application of selectively acylated glycosides for the alpha-galactosidase-catalyzed synthesis of disaccharides
Jazyk angličtina Země Spojené státy americké Médium print
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
12879742
DOI
10.1007/bf02931362
Knihovny.cz E-zdroje
- MeSH
- alfa-galaktosidasa chemie metabolismus MeSH
- Burkholderia cepacia enzymologie MeSH
- disacharidy biosyntéza chemická syntéza MeSH
- katalýza MeSH
- konformace sacharidů MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární struktura MeSH
- nitrofenylgalaktosidy biosyntéza chemická syntéza MeSH
- rozpouštědla MeSH
- sacharidové sekvence MeSH
- Talaromyces enzymologie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- alfa-galaktosidasa MeSH
- disacharidy MeSH
- nitrofenylgalaktosidy MeSH
- rozpouštědla MeSH
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.
