title: Glycosidation of fructose-containing disaccharides using MCM-41 material as the catalyst.
abstract: 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.
authors.affiliation: Merck Sharp and Dohme BV, Waarderweg 39, NL-2031 BN Haarlem, The Netherlands.
authors.forename: Anneke M
authors.initials: AM
authors.lastname: van der Heijden
authors.forename: Tsz Chung
authors.initials: TC
authors.lastname: Lee
authors.forename: Fred
authors.initials: F
authors.lastname: van Rantwijk
authors.forename: Herman
authors.initials: H
authors.lastname: van Bekkum
mesh_terms: 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
chemical_list: 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