Conformational flexibility in highly sulfated beta-D-glucopyranoside derivatives.
Triggered by findings on heparin-like disaccharides, the conformation of sulfated glucopyranosides was investigated. Sodium (methyl 2,3,4-tri-O-sulfonato-beta-D-glucopyranosid)uronate tetrasodium salt is in a conformational equilibrium, to which a non-chair conformation contributes. The same is true for methyl (methyl 2,3,4-tri-O-sulfonato-beta-D-glucopyranosid)uronate trisodium salt, methyl 2,3,4,6-tetra-O-sulfonato-beta-D-glucopyranoside tetrasodium salt, and octa-O-sulfonato-beta, beta-trehalose octasodium salt, with less obvious non-chair contributions. The effect is charge related. The conformational effect, which does not occur in analogous alpha-D-glucopyranoside derivatives, is discussed in terms of the anomeric effect.
Wessel
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F. Hoffmann-La Roche Ltd, Pharma Division, Basel, Switzerland.
Bartsch
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D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005960:Glucosides / Q000737:chemistry*; D005965:Glucuronates / Q000737:chemistry; D020723:Glucuronic Acid; D006025:Glycosaminoglycans / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry*; D013431:Sulfates / Q000737:chemistry*
D005960:Glucosides; D005965:Glucuronates; D006025:Glycosaminoglycans; D009844:Oligosaccharides; D013431:Sulfates; D020723:Glucuronic Acid