Synthesis of 1',6'-disubstituted sucroses and their behavior as glucosyl donors for a microbial alpha-glucosyltransferase.
Versatile 6'-chloro-6'-deoxy-1'-substituted sucrose derivatives were synthesized in search of an optimum donor substrate for the intermolecular transglucosylation with the alpha-glucosyltransferase from Protaminobacter rubrum. Two substituents at the C-1' and C-6' positions of sucrose were introduced utilizing the distinct reactivity of the corresponding sulfonates. Methyl beta-D-arabinofuranoside was most efficiently glucosylated with the 1'-deoxy derivative 5. Hydroxyl and fluoro groups at C-1' show a tendency to enhance the intramolecular transglucosylations, giving 3-O-(alpha-D-glucopyranosyl)-D-fructose derivatives.
Kakinuma
H
H
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
Yuasa
H
H
Hashimoto
H
H
D001419:Bacteria / Q000201:enzymology*; D001420:Bacteria, Aerobic / Q000201:enzymology*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005964:Glucosyltransferases / Q000378:metabolism*; D007202:Indicators and Reagents; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013379:Substrate Specificity; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism
D007202:Indicators and Reagents; D013395:Sucrose; D005964:Glucosyltransferases