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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
Brena, Beatriz M.
Jimeno, M. Luisa
|Keywords:||Galactosyl derivatives, transgalactosylation, lactose, polyols, enzymatic synthesis, immobilized β-galactosidase|
|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|
|Appears in Collections:||(CENQUIOR) Artículos|
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