Glucosylation of alpha-butyl- and alpha-octyl-D-glucopyranosides by dextransucrase and alternansucrase from Leuconostoc mesenteroides.
For the first time, glucosylation of alpha-butyl- and alpha-octylglucopyranoside was achieved using dextransucrase (DS) of various specificities, and alternansucrase (AS) from Leuconostoc mesenteroides. All the glucansucrases (GS) tested used alpha-butylglucopyranoside as acceptor; in particular, DS produced alpha-D-glucopyranosyl-(1-->6)-O-butyl-alpha-D-glucopyranoside and alpha-D-glucopyranosyl-(1-->6)-alpha-D-glucopyranosyl-(1-->6)-O-butyl-alpha-D-glucopyranoside. In contrast, alpha-octylglucopyranoside was glucosylated only by AS which was shown to be the most efficient catalyst. The conversion rates, obtained with this enzyme at sucrose to acceptor molar ratio of 2:1 reached 81 and 61% for alpha-butylglucopyranoside and alpha-octylglucopyranoside, respectively. Analyses obtained from liquid chromatography coupled with mass spectrometry revealed that different series of alpha-alkylpolyglucopyranosides regioisomers of increasing polymerization degree can be formed depending on the specificity of the catalyst.
Richard
Gaëtan
G
Département de Génie Biochimique et Alimentaire, Centre de Bioingénierie Gilbert Durand, UMR CNRS 5504, UMR INRA 792, INSA, 135 Avenue de Rangueil, 31077 Toulouse 4, France.
Morel
Sandrine
S
Willemot
René-Marc
RM
Monsan
Pierre
P
Remaud-Simeon
Magali
M
D002851:Chromatography, High Pressure Liquid; D005964:Glucosyltransferases / Q000378:metabolism*; D006027:Glycosides / Q000737:chemistry* / Q000378:metabolism*; D006031:Glycosylation; D016695:Glycosyltransferases / Q000378:metabolism*; D007934:Leuconostoc / Q000201:enzymology*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D006027:Glycosides; D016695:Glycosyltransferases; D005964:Glucosyltransferases; C033837:alternansucrase; C020025:dextransucrase