Characterization of galactosyl derivatives obtained by transgalactosylation of lactose and different polyols using immobilized beta-galactosidase from Aspergillus oryzae.
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 galactoside. 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 beta-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 ((1)H and (13)C) and 2D (gCOSY, TOCSY, multiplicity-edited gHSQC, and gHMBC) NMR experiments. The beta-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.
Irazoqui
Gabriela
G
Departamento de Biociencias, Facultad de Química, Universidad de la República, Montevideo, Uruguay.
Giacomini
Cecilia
C
Batista-Viera
Francisco
F
Brena
Beatriz M
BM
Cardelle-Cobas
Alejandra
A
Corzo
Nieves
N
Jimeno
María Luisa
ML
D001236:Aspergillus oryzae / Q000737:chemistry / Q000201:enzymology*; D004800:Enzymes, Immobilized / Q000737:chemistry / Q000378:metabolism*; D005656:Fungal Proteins / Q000737:chemistry / Q000378:metabolism*; D005697:Galactosides / Q000737:chemistry* / Q000378:metabolism; D007785:Lactose / Q000378:metabolism*; D011108:Polymers / Q000378:metabolism*; D013237:Stereoisomerism; D001616:beta-Galactosidase / Q000737:chemistry / Q000378:metabolism*
D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D005697:Galactosides; D011108:Polymers; C024617:polyol; D001616:beta-Galactosidase; D007785:Lactose