Chemical and enzymatic synthesis of fructose analogues as probes for import studies by the hexose transporter in parasites
| Autor: | Casimir Blonski, Frédéric Bringaud, Laurent Azema, Jacques Périé |
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| Rok vydání: | 2000 |
| Předmět: |
Magnetic Resonance Spectroscopy
Monosaccharide Transport Proteins Stereochemistry Clinical Biochemistry Trypanosoma brucei brucei Pharmaceutical Science Fructose-bisphosphate aldolase Fructose Biochemistry Mass Spectrometry chemistry.chemical_compound Amadori rearrangement Drug Discovery Glucose import Animals Molecular Biology Hexose transport Dihydroxyacetone phosphate biology Muscles Organic Chemistry Aldolase A Glucose transporter Biological Transport chemistry Molecular Probes biology.protein Molecular Medicine Rabbits |
| Zdroj: | Bioorganicmedicinal chemistry. 8(4) |
| ISSN: | 0968-0896 |
| Popis: | Various D-fructose analogues modified at C-1 or C-6 positions were synthesized from D-glucose by taking advantage of the Amadori rearrangement or using the aldol condensation between dihydroxyacetone phosphate and appropriate aldehyde catalyzed by fructose 1,6-diphosphate aldolase from rabbit muscle. The affinities of the analogues for the glucose transporter expressed in the mammalian form of Trypanosoma brucei were determined by inhibition of radiolabelled 2-deoxy-D-glucose (2-DOG) transport using zero-trans kinetic analysis. Interestingly, the analogues bearing an aromatic group (i.e. a fluorescence marker) at C-1 or C-6 positions present comparable apparent affinities to D-fructose for the transporter. This result could find applications for hexose transport studies and also provides criteria for the design of glucose import inhibitors. |
| Databáze: | OpenAIRE |
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