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Title

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

AuthorsIrazoqui, Gabriela; Giacomini, Cecilia; Batista-Viera, Francisco; Brena, Beatriz M.; Cardelle-Cobas, Alejandra CSIC ORCID; Corzo, Nieves CSIC ORCID ; Jimeno, M. Luisa CSIC ORCID
KeywordsGalactosyl derivatives
transgalactosylation
lactose
polyols
enzymatic synthesis
immobilized β-galactosidase
Issue Date2009
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 57 (23) : 11302–11307 (2009)
AbstractThe 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
URIhttp://hdl.handle.net/10261/34478
DOI10.1021/jf901834k
ISSN0021-8561
Appears in Collections:(CENQUIOR) Artículos

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