Glycosidation of fructose-containing disaccharides using MCM-41 material as the catalyst.
Glycosidation of saccharides combines the essential characteristics of two major renewable classes, viz. triglycerides and carbohydrates, leading to biofriendly surfactants and emulsifiers. The development of the alkylglycosides derived from reducing disaccharides has lagged, because no efficient synthesis was available. We have found that ordered mesoporous materials of the MCM-41 type are active and selective catalysts for the glycosidation of disaccharides containing fructose at the reducing end, i.e., isomaltulose, lactulose and leucrose. No alcoholysis or hydrolysis of the glycosidic bond was observed, demonstrating the mildness of the MCM-41 catalyst. Leucrose was found to be less reactive than the two other disaccharides, in accordance with the absence of furanose forms in leucrose.
van der Heijden
Anneke M
AM
Merck Sharp and Dohme BV, Waarderweg 39, NL-2031 BN Haarlem, The Netherlands.
Lee
Tsz Chung
TC
van Rantwijk
Fred
F
van Bekkum
Herman
H
D000535:Aluminum / Q000737:chemistry; D002384:Catalysis; D004187:Disaccharides / Q000737:chemistry*; D005079:Excipients / Q000737:chemistry; D005632:Fructose; D006026:Glycoside Hydrolases / Q000737:chemistry*; D007534:Isomaltose / Q000031:analogs & derivatives* / Q000737:chemistry; D007792:Lactulose / Q000737:chemistry; D012825:Silicon / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry
D004187:Disaccharides; D005079:Excipients; D013501:Surface-Active Agents; D005632:Fructose; D007792:Lactulose; D007534:Isomaltose; D000535:Aluminum; D006026:Glycoside Hydrolases; C008189:isomaltulose; C060525:leucrose; D012825:Silicon