Synthesis and evaluation of fructose analogues as inhibitors of the D-fructose transporter GLUT5

A Tatibouet, J Yang, C Morin, G D Holman

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We have examined the specificity and binding-site spatial requirements of the fructose transporter GLUT5. Interaction with a series of fructofuranosides and fructopyranosides suggests that both furanose and pyranose ring forms of D-fructose combine with GLUT5. The epimers of D-fructose all have low affinity for GLUT5 suggesting that the transporter requires all hydroxyls to be in the fructo-configuration. Similarly there is poor tolerance of all allyl derivatives of D-fructose except 6-O-allyl-D-fructo-furanose. Therefore, the C-6 position offers the most suitable position for development of affinity probes and labels for exploring GLUT5 biochemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)1825-1833
Number of pages9
JournalBioorganic and Medicinal Chemistry
Issue number7
Publication statusPublished - 2000


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