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Application of Selectively Acylated Glycosides for the Alpha-Galactosidase-Catalyzed Synthesis of Disaccharides

Application of Selectively Acylated Glycosides for the Alpha-Galactosidase-Catalyzed Synthesis of Disaccharides

P Simerská, M Kuzma, A Pisvejcová, L Weignerová, M Macková, S Riva, V Kren

Folia Microbiol (Praha). 2003;48(3):329-37.

PMID: 12879742

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7493950	4-Nitrophenyl α-D-galactopyranoside		7493-95-0	Price

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