Abstract
4-Nitrophenyl α-d-galactopyranosyl-(1→3)-6-O-acetyl-α-d-galactopyranoside was prepared in a transglycosylation reaction catalyzed by α-d-galactosidase fromTalaromyces flavus using 4-nitrophenyl α-d-galactopyranoside as a glycosyl donor and 4-nitrophenyl 6-O-acetyl-α-d-galactopyranoside as an acceptor. 4-Nitrophenyl 6-O-acetyl-α-d-galactopyranoside and 4-nitrophenyl 6-O-acetyl-β-d-galactopyranoside were prepared in a regioselective enzymic transesterification in pyridine-acetone catalyzed by the lipase PS fromBurkholderia 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 α-galactosidase fromT. 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.
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This work was supported byCzech National Science Foundation grants no. 203/01/1018 and 204/02/P096.Institutional Research Concept AV OZ 502 0903, COST D25/0001/02 and by bilateral projectConsiglio Nazionale delle Ricerche-Acad. Sci. Czech Rep.
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Simerská, P., Kuzma, M., Pišvejcová, A. et al. Application of selectively acylated glycosides for the α-galactosidase-catalyzed synthesis of disaccharides. Folia Microbiol 48, 329–337 (2003). https://doi.org/10.1007/BF02931362
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DOI: https://doi.org/10.1007/BF02931362