D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter, GLUT5.
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.
Tatibouët
A
A
Institut de Chimie Organique et Analytique, Université d'Orléans, BP 6759, F-45067, Orleans, France. arnaud.tatibouet@univ-orleans.fr
Lefoix
M
M
Nadolny
J
J
Martin
O R
OR
Rollin
P
P
Yang
J
J
Holman
G D
GD
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
C438057:5-thio-fructose; D002250:Carbon Radioisotopes; D051296:Glucose Transporter Type 5; D009004:Monosaccharide Transport Proteins; D005632:Fructose; D013013:Sorbose