title: D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter, GLUT5.
abstract: Epimerisation and subsequent functionalization at C-5 of D-fructopyranose derivatives under Mitsunobu and Garegg's conditions provided efficient access to 5-thio-D-fructose (2) as well as to 5-azido-5-deoxy-1,2-O-isopropylidene-beta-D-fructopyranose (19), a known precursor to 2,5-deoxy-2,5-imino-D-mannitol (3). The interaction of 2 with the D-fructose transporter GLUT5, was found to be weaker than that of D-fructose, a result that suggests involvement of the ring oxygen atom in the recognition of D-fructose by GLUT5.
authors.affiliation: Institut de Chimie Organique et Analytique, Université d'Orléans, BP 6759, F-45067, Orleans, France. arnaud.tatibouet@univ-orleans.fr
authors.forename: A
authors.initials: A
authors.lastname: Tatibouët
authors.forename: M
authors.initials: M
authors.lastname: Lefoix
authors.forename: J
authors.initials: J
authors.lastname: Nadolny
authors.forename: O R
authors.initials: OR
authors.lastname: Martin
authors.forename: P
authors.initials: P
authors.lastname: Rollin
authors.forename: J
authors.initials: J
authors.lastname: Yang
authors.forename: G D
authors.initials: GD
authors.lastname: Holman
mesh_terms: D000818:Animals; D001665:Binding Sites; D016466:CHO Cells; D002250:Carbon Radioisotopes; D006224:Cricetinae; D005632:Fructose / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D051296:Glucose Transporter Type 5; D009004:Monosaccharide Transport Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D011485:Protein Binding; D013013:Sorbose / Q000737:chemistry* / Q000378:metabolism
chemical_list: C438057:5-thio-fructose; D002250:Carbon Radioisotopes; D051296:Glucose Transporter Type 5; D009004:Monosaccharide Transport Proteins; D005632:Fructose; D013013:Sorbose