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Closed Access item Characterization of Galactosyl Derivatives Obtained by Transgalactosylation of Lactose and Different Polyols Using Immobilized beta-Galactosidase from Aspergillus oryzae

Authors:Irazoqui, Gabriela
Giacomini, Cecilia
Batista-Viera, Francisco
Brena, Beatriz M.
Cardelle-Cobas, Alejandra
Corzo, Nieves
Jimeno, M. Luisa
Keywords:Galactosyl derivatives, transgalactosylation, lactose, polyols, enzymatic synthesis, immobilized β-galactosidase
Issue Date:2009
Publisher:American Chemical Society
Citation:Journal of Agricultural and Food Chemistry 57 (23) : 11302–11307 (2009)
Abstract:The synthesis of novel galactosides is interesting because of their important role in several biological processes. Their properties greatly depend upon the configuration and type of galacto- side. Therefore, to study biological activity, it is essential to elucidate the structure of the products. Glycosidases are capable of catalyzing glycosidic linkages with absolute stereoselectivity of the anomeric center. We report the enzymatic synthesis of galactosyl-ethylene glycol, galactosyl- glycerol, and galactosyl-erythritol by immobilized β-galactosidase from Aspegillus oryzae. The obtained galactosides were isolated and fully characterized by an extensive nuclear magnetic resonance (NMR) study. Complete structure elucidation and full proton and carbon assignments were carried out using 1D (1H and 13C) and 2D (gCOSY, TOCSY, multiplicity-edited gHSQC, and gHMBC) NMR experiments. The β-galactosidase from A. oryzae showed a strong preference for primary alcohols. For galactosyl-glycerol and galactosyl-erythritol, this preference generated one and two chiral centers, respectively, and a mixture of stereoisomers was obtained as a consequence.
Publisher version (URL):http://dx.doi.org/10.1021/jf901834k
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