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D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter, GLUT5


Reference:

Tatibouet, A., Lefoix, M., Nadolny, J., Martin, O. R., Rollin, P., Yang, J. and Holman, G. D., 2001. D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter, GLUT5. Carbohydrate Research, 333 (4), pp. 327-334.

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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 GLUTS, 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 GLUTS. (C) 2001 Elsevier Science Ltd. All rights reserved.

Details

Item Type Articles
CreatorsTatibouet, A., Lefoix, M., Nadolny, J., Martin, O. R., Rollin, P., Yang, J. and Holman, G. D.
DepartmentsFaculty of Science > Biology & Biochemistry
RefereedYes
StatusPublished
ID Code4299
Additional InformationID number: ISI:000170059100007

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