Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of D-glucose and D-altrose and assessment of their erythrocyte transmembrane transport

Stefano Bresciani; Tomas Lebl; Alexandra M Z Slawin; David O'Hagan

doi:10.1039/c0cc01128b

Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of D-glucose and D-altrose and assessment of their erythrocyte transmembrane transport

Chem Commun (Camb). 2010 Aug 14;46(30):5434-6. doi: 10.1039/c0cc01128b. Epub 2010 Jun 7.

Authors

Stefano Bresciani¹, Tomas Lebl, Alexandra M Z Slawin, David O'Hagan

Affiliation

¹ University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, KY16 9ST, UK.

PMID: 20532277
DOI: 10.1039/c0cc01128b

Abstract

The 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of d-glucose and d-altrose were prepared and characterised and these novel sugar analogues were explored by 2D-(19)F-EXSY NMR for their potential to cross erythrocyte (red blood cell) membranes, by comparison with the well known capacity of erythrocytes to transport d-glucose.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cell Membrane Permeability
Crystallography, X-Ray
Erythrocytes / metabolism*
Glucose / chemical synthesis
Glucose / chemistry*
Glucose / metabolism*
Halogenation*
Hexoses / chemical synthesis
Hexoses / chemistry*
Hexoses / metabolism*
Humans
Models, Molecular
Nuclear Magnetic Resonance, Biomolecular

Substances

Hexoses
Glucose