Beta-galactosidase catalyzed selective galactosylation of aromatic compounds.
A new approach to galacto-oligosaccharides and galacto-conjugates synthesis performed by the beta-galactosidase from Kluyveromyces lactis is reported. The enzymatic galactosylation of eight kinds of adsorbed aromatic primary alcohols, in particular the two drugs guaifenesin and chlorphenesin, gave the corresponding beta-D-galacto-pyranosides in yields ranging between approximately 10% and 96%. For the first time, we have showed that the adsorption of acceptor substrates onto solid supports such as silica gel influences the yield and the selectivity of galacto-conjugates synthesis. In particular, we observed that adsorption of acceptor favored the synthesis of digalactosylated compounds.
Bridiau
Nicolas
N
Laboratoire de Biotechnologie et de Chimie Bio-organique, CNRS FRE 2766, Université de La Rochelle, Avenue Michel Crépeau, 17042 La Rochelle, France.
Taboubi
Selma
S
Marzouki
Nejib
N
Legoy
Marie Dominique
MD
Maugard
Thierry
T
D000327:Adsorption; D002384:Catalysis; D002743:Chlorphenesin / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D006140:Guaifenesin / Q000737:chemistry / Q000378:metabolism; D006841:Hydrocarbons, Aromatic / Q000737:chemistry / Q000378:metabolism*; D007716:Kluyveromyces / Q000201:enzymology*; D015394:Molecular Structure; D001616:beta-Galactosidase / Q000378:metabolism*
D006841:Hydrocarbons, Aromatic; D006140:Guaifenesin; D001616:beta-Galactosidase; D002743:Chlorphenesin