Insights into stereochemical features of sulphated carbohydrates: X-ray crystallographic and modelling investigations

The three-dimensional structures of the 2-, 3-, 4- and 6-monosulphatesof methyl -D-galactopyranoside have been determined by X-raycrystallography; the first two as the sodium salt, the thirdas both the sodium and potassium salts, and the fourth as apotassium salt. These represent the principal sulphated monomersof the carrageenan polysaccharides. The results extend our knowledgeof the stereochemical features, such as ring conformation, sulphategeometry, hydrogen bonding and cation co-ordination, which characterizesulphated monosaccharides. The stereochemical data have beenused to derive a mean geometry of the O-sulphate group and aset of force constants for use in molecular mechanics calculationson sulphated monosaccharides. These may be used in an extrapolationof the populations of stable conformers of related oligo- andpolysaccharides. crystal structures molecular mechanics O-sulphated carbohydrates X-ray diffraction