Synthesis of O-β-galactopyranosyl-L-serine derivatives using β-galactosidase in aqueous-organic reaction systems

Article abstract of DOI:10.1080/07328309908543986

The galactosylation of amino protected serine methyl ester derivatives by β -galactosidases from E. coli and A. oryzae in aqueous-organic solvents was investigated. A comparison of enzyme activity in aqueous buffer and in several aqueous-organic mixtures revealed that the presence of an organic solvent normally causes a loss in enzyme activity. When the enzyme is used in suspensions with mainly undissolved lactose, the detrimental influence of an organic solvent is less marked if it does not exceed 25 % of the added mixture with water. Employing organic cosolvents, such as acetonitrile, 2-butanone, acetone or ethyl acetate, we obtained yields of the desired galactosylation products higher than those with the enzyme in purely aqueous solution. The amino protecting group shows a significant influence on the transglycosylation reaction in terms of yield, the best up to 28 % being achieved in the synthesis of Aloc-(Ga1β1-)Ser-OMe with β-galactosidase from E. coli in a reaction mixture containing 8 to 15 % organic solvent.

Full text of DOI:10.1080/07328309908543986

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Synthesis of O-β-Galactopyranosyl-
L-Serine Derivatives Using β-
Galactosidase in Aqueous-Organic
Reaction Systems
K.-C. Becker & P. Kuhl
a CHEMTEC LEUNA GmbH, Am Haupttor , 06236 Leuna,
Germany
b Institute of Biochemistry, Dresden University of
Technology , 01062 Dresden, Germany
Published online: 27 Feb 2008.
To cite this article: K.-C. Becker & P. Kuhl (1999) Synthesis of O-β-Galactopyranosyl-L-
Serine Derivatives Using β-Galactosidase in Aqueous-Organic Reaction Systems, Journal of
Carbohydrate Chemistry, 18:2, 121-129, DOI: 10.1080/07328309908543986
To link to this article: http://dx.doi.org/10.1080/07328309908543986
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