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Conformational differences between Fuc(alpha 1-3) GlcNAc and its thioglycoside analogue
B Aguilera1, J Jiménez-Barbero, A Fernández-Mayoralas
1Departmento de Química Orgánica Biológica, Instituto de Química Orgánica, CSIC, Madrid, Spain.
Carbohydrate Research
|July 24, 1998
Summary
Nuclear Overhauser Effect (NOE) measurements and molecular mechanics revealed distinct solution behaviors for a thioglycoside analogue compared to its natural O-disaccharide counterpart. The S-analogue exhibits two conformational families (syn and anti), unlike the natural form’s single conformation.
Area of Science:
- Carbohydrate Chemistry
- Structural Biology
- Computational Chemistry
Background:
- Understanding the conformational dynamics of disaccharides is crucial for their biological functions.
- Fuc(alpha 1-3)GlcNAc is a key disaccharide motif with implications in biological recognition.
Purpose of the Study:
- To investigate and compare the solution-state conformational behavior of the natural Fuc(alpha 1-3)GlcNAc disaccharide and its thioglycoside S-analogue.
- To elucidate the structural differences induced by the substitution of oxygen with sulfur in the glycosidic linkage.
Main Methods:
- Nuclear Overhauser Effect (NOE) measurements were employed to gather experimental structural data in solution.
- Molecular mechanics calculations were utilized to model and analyze the conformational landscapes of both compounds.
Main Results:
- The natural Fuc(alpha 1-3)GlcNAc O-disaccharide predominantly adopts a single, stable conformation in solution.
- The thioglycoside S-analogue displays a more flexible conformational profile, existing in two distinct families: 'syn' and 'anti'.
Conclusions:
- The replacement of the glycosidic oxygen with sulfur significantly alters the conformational dynamics of the disaccharide.
- The S-analogue's dual conformational states may have implications for its binding properties and biological activity compared to the natural O-disaccharide.