Synthesis of 1',6'-disubstituted sucroses and their behavior as glucosyl donors for a microbial α-glucosyltransferase

Article abstract of DOI:10.1016/0008-6215(96)00002-X

Versatile 6'-chloro-6'-deoxy-1'-substituted sucrose derivatives were synthesized in search of an optimum donor substrate for the intermolecular transglucosylation with the α-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 β-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-(α-D-glucopyranosyl)-D-fructose derivatives.