Transglycosylation reactions employing .beta.-galactosidase

Details Transglycosylation reactions employing .beta.-galactosidase Transglycosylation reactions employing .beta.-galactosidase

1996-10-17

1999-03-02

Prats, Francisco

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing compound containing saccharide radical

435 97, 435100, 435101, 435 74, 435207, 536 178, C12P 1914, C12P 1918, C12P 1904, C12N 938

Patent

active

058769811

ABSTRACT:
.beta.-Galactosides are synthesized using a transglycosylation reaction catalyzed by .beta.-galactosidase. The reaction employs a carbohydrate donor having a glycosidic leaving group attached to its anomeric carbon and an oxo group attached to the C-6 carbon. Strong leaving groups are preferred over weak leaving groups. The method can be carried out in aqueous solution without organic solvents to give the transglycosylation product in high yields and high regioselectivity. The synthesis of lactosamine using this methodology with galactose oxidase (GO) and .beta.-galactosidase has been accomplished. (FIG. 3). The methodology affords simple reaction conditions and minimal purification steps. In addition, the intermediate substrates maintain high stability, the process affords high yields and the enzymes and reagents employed are commercially available with high stability and low costs.

REFERENCES:
patent: 5104797 (1992-04-01), Mazur et al.
patent: 5532147 (1996-07-01), Nilsson
Chemical Abstracts 119(17):179341n, 1993.
Angew. Chem., Int'l Ed. 35(20):2348-2350, 1996.
Lee et al, Anal. Biohem. 216:358-364, 1994.
Toone et al, Tetrahedron 45(17):5397-5405, 1989.

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