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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter,
A Tatibouët1, M Lefoix, J Nadolny
1Institut de Chimie Organique et Analytique, Université d'Orléans, BP 6759, F-45067, Orleans, France. arnaud.tatibouet@univ-orleans.fr
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.
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