Process for induction of intramolecular migration of sulfates, phosphates, and other oxyanions
AssigneeNeoparin, Inc.
InventorsSteven Guo, H. Conrad
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Abstract
This present invention provides methods for structural modification of a molecule containing a hydroxyl group and an oxyanion amide or oxyanion ester group on adjacent or nearby atomic positions. The oxyanion, such as sulfate and phosphate, can be transferred to the hydroxyl group when the molecule is treated with a carbodiimide or various other oxyanion activating agents, resulting in selective oxyanion transfer to the hydroxyl group. Certain polysaccharides, and especially glycosaminoglycans, may be sulfated at a specific hydroxyl group when such hydroxyl group is present adjacent to or nearby a sulfate, phosphate, or other oxyanionic group in ester- or amide-linked forms.
Claims45
A process for structural modification of a substrate molecule comprising an oxyanion in an amide or ester linkage and a hydroxyl group wherein the oxyanion is caused to undergo regioselective intramolecular migration to the hydroxyl group, said process comprising:
- a) converting said substrate molecule into an amine salt;
- b) dissolving the amine salt of said substrate molecule in an aprotic solvent to form a solution;
- and
- c) treating said solution with an activating agent to cause said oxyanion to regioselectively migrate to said hydroxyl group.
A composition of polysaccharides, oligosaccharide and monosaccharide containing an amino sugar, which amino sugar contains the hydroxyloxyanion, such as sulfate and phosphate, in the range from 0.01 moles to 1.00 moles of hydroxyl oxianion per amino sugar.
Dependencies are inferred from the claim text.