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Updated: Aug 6, 2026
14:18
A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
D-Fructose-L-sorbose interconversions. Access to 5-thio-D-fructose and interaction with the D-fructose transporter,
A Tatibouët1, M Lefoix, J Nadolny
1Institut de Chimie Organique et Analytique, Université d'Orléans, BP 6759, F-45067, Orleans, France. arnaud.tatibouet@univ-orleans.fr
Carbohydrate Research
|July 17, 2001
Summary
Researchers synthesized 5-thio-D-fructose and a precursor to 2,5-deoxy-2,5-imino-D-mannitol. The synthesized thio-fructose binds less effectively to the D-fructose transporter GLUT5, suggesting the ring oxygen is crucial for D-fructose recognition.
Area of Science:
- Carbohydrate Chemistry
- Biochemistry
- Molecular Transport
Background:
- D-fructose is a key monosaccharide metabolized in the body.
- The D-fructose transporter GLUT5 mediates fructose uptake in various tissues.
- Understanding fructose transport mechanisms is vital for metabolic research.
Purpose of the Study:
- To synthesize novel D-fructose derivatives, specifically 5-thio-D-fructose.
- To investigate the interaction of these derivatives with the GLUT5 transporter.
- To elucidate the role of specific structural features in GLUT5 recognition.
Main Methods:
- Epimerization and functionalization of D-fructopyranose derivatives.
- Mitsunobu and Garegg's reaction conditions for synthesis.
- Assessing the binding affinity of synthesized compounds to GLUT5.
Main Results:
- Efficient synthesis of 5-thio-D-fructose and a precursor to 2,5-deoxy-2,5-imino-D-mannitol.
- 5-thio-D-fructose exhibited weaker interaction with GLUT5 compared to D-fructose.
- This suggests the D-fructose ring oxygen atom is important for transporter recognition.
Conclusions:
- Novel synthetic routes to functionalized D-fructose derivatives were established.
- The study provides insights into the molecular recognition mechanism of GLUT5.
- The findings highlight the significance of the ring oxygen in D-fructose binding to GLUT5.
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