Enzymatic transformations in supersaturated substrate solutions: II. Synthesis of disaccharides via transglycosylation.
Enzymatic transglycosylation in supersaturated solutions of substrates was investigated using crude glycosidase preparations from barley, snail, and coffee beans. It was shown that the use of supersaturated glycoside solutions as media for transglycosylation reactions offers considerable advantages over conventional aqueous systems. These advantages include higher yields, more efficient use of the donor glycosides and improved volumetric productivity, especially in the case of poorly water-soluble substrates. The regioselectivity of the glycosylation was not significantly affected by high concentrations of acceptor glycosides. It was also shown that the regioselectivity of transfer could be directed towards secondary hydroxyl groups by the use of methyl 6-O-acetyl-alpha-galactopyranoside as acceptor. The value of these approaches was demonstrated by the synthesis of methyl 3- and 4-O-beta-D-galactopyranosyl-alpha-D-galactopyranosides and methyl 3-O-beta-D-galactopyranosyl-alpha-L-fucopyranoside on a preparative scale.
Millqvist-Fureby
A
A
Department of Macromolecular Sciences, Institute of Food Research, Earley Gate, Whiteknights Road, Reading RG6 6BZ, UK.
MacManus
D A
DA
Davies
S
S
Vulfson
E N
EN
D002236:Carbohydrate Conformation; D003069:Coffee / Q000201:enzymology; D004187:Disaccharides / Q000138:chemical synthesis*; D006031:Glycosylation; D001467:Hordeum; D007202:Indicators and Reagents; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D012996:Solutions; D013379:Substrate Specificity; D000519:alpha-Galactosidase / Q000378:metabolism*; D001614:beta-Amylase / Q000378:metabolism*
D003069:Coffee; D004187:Disaccharides; D007202:Indicators and Reagents; D012996:Solutions; D008049:Lipase; D001614:beta-Amylase; D000519:alpha-Galactosidase