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

A Tatibouet, M Lefoix, J Nadolny, O R Martin, P Rollin, J Yang, G D Holman

Research output: Contribution to journalArticle

19 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)327-334
Number of pages8
JournalCarbohydrate Research
Volume333
Issue number4
Publication statusPublished - 2001

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Glucose Transporter Type 5
Sorbose
Fructose
Mannitol
Oxygen
Derivatives
Atoms
5-thio-fructose

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D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter, GLUT5. / Tatibouet, A; Lefoix, M; Nadolny, J; Martin, O R; Rollin, P; Yang, J; Holman, G D.

In: Carbohydrate Research, Vol. 333, No. 4, 2001, p. 327-334.

Research output: Contribution to journalArticle

Tatibouet, A, Lefoix, M, Nadolny, J, Martin, OR, Rollin, P, Yang, J & Holman, GD 2001, 'D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter, GLUT5', Carbohydrate Research, vol. 333, no. 4, pp. 327-334.
Tatibouet, A ; Lefoix, M ; Nadolny, J ; Martin, O R ; Rollin, P ; Yang, J ; Holman, G D. / D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter, GLUT5. In: Carbohydrate Research. 2001 ; Vol. 333, No. 4. pp. 327-334.
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