Oxime-linked polysaccharides and methods of preparing the same
View Patent ↗Polysaccharides comprising one or more oxime linkages are provided. Methods for their preparation include the polycondensation of saccharides bearing oxime-forming substituents. In some embodiments, polymerization is conducted in the presence of galactose oxidase. The resulting oxime-linked polysaccharides have desirable properties and are useful in numerous applications including paper manufacturing and drug delivery vehicles.
1. A polysaccharide of Formula I:
wherein:
A is, independently, a monosaccharide, disaccharide, trisaccharide, or low molecular weight polysaccharide residue; and
n is about 4 to about 10,000.
2. A polysaccharide of claim 1 wherein said monosaccharide residue is derived from galactose.
3. A polysaccharide of claim 1 wherein said disaccharide residue is derived from lactose, melibiose, or galactosyl arabinose.
4. A polysaccharide of claim 1 wherein said low molecular weight polysaccharide residue is derived from degraded galactomannan gum.
5. A polysaccharide of claim 4 wherein said degraded galactomannan gum comprises guar, tara, fenugreek, or locust bean gum.
6. A polysaccharide of claim 1 wherein said low molecular weight polysaccharide has a M w of from about 500 to about 5000 daltons.
7. A polysaccharide comprising at least one oxime linkage and having a weight average molecular weight of at least about 1000 daltons.
8. A polysaccharide of claim 7 having a weight average molecular weight of at least about 4000 daltons.
9. A polysaccharide of claim 7 which comprises a plurality of saccharide residues selected from the group consisting of monosaccharide, disaccharide, trisaccharide, and low molecular weight polysaccharide residues.
10. A polysaccharide of claim 9 wherein said monosaccharide residue is derived from galactose.
11. A polysaccharide of claim 9 wherein said disaccharide residue is derived from lactose, melibiose, or galactosyl arabinose.
12. A polysaccharide of claim 9 wherein said low molecular weight polysaccharide residue is derived from degraded galactomannan gum.
13. A polysaccharide of claim 12 wherein said degraded galactomannan gum comprises guar, tara, fenugreek, or locust bean gum.
14. A process for preparing a polysaccharide comprising at least one oxime linkage, said process comprising contacting a first saccharide with a second saccharide in the presence of galactose oxidase, wherein each of said saccharides comprises at least one —ONH 2 functionality and at least one —CH 2 OH functionality oxidizable by said galactose oxidase.
15. A process of claim 14 wherein said saccharides are derived from galactose.
16. A process of claim 14 wherein said saccharides are derived from lactose, melibiose, or galactosyl arabinose.
17. A process of claim 14 wherein said saccharides are derived from degraded galactomannan gum.
18. A process of claim 17 wherein said degraded galactomannan gum comprises guar, tara, fenugreek, or locust bean gum.
19. A process of claim 14 wherein said saccharides comprise terminal or pendant moieties capable of being oxidized by said galactose oxidase.
20. A process of claim 14 wherein said polysaccharide has a weight average molecular weight of at least about 1000 daltons.
21. A process of claim 14 wherein said polysaccharide has a weight average molecular weight of at least about 4000 daltons.
22. A polysaccharide comprising at least two oxime linkages prepared by the process of claim 14 .
23. A process of preparing a polysaccharide comprising at least one oxime linkage, said process comprising contacting a first saccharide with a second saccharide, wherein each of said saccharides comprises at least one —ONH 2 functionality and at least one precursor to a —CHO functionality, and converting said precursor to said —CHO functionality.
24. A process of claim 23 wherein said precursor comprises a —CH 2 OH functionality which is oxidized to a —CHO functionality.
25. A process of claim 24 wherein said oxidation comprises enzymatic oxidation.
26. A polysaccharide comprising at least two oxime linkages prepared by the process of claim 23 .
27. A process of preparing a polysaccharide comprising at least one oxime linkage, said process comprising contacting a first saccharide with a second saccharide, wherein each of said saccharides comprises at least one —CHO functionality and at least one —ONH 2 functionality.
28. A polysaccharide comprising at least two oxime linkages prepared by the process of claim 27 .
29. A polymer composition comprising the polysaccharide of claim 1 and paper pulp.
30. A flucculant comprising the polysaccharide of claim 1 .
31. A retention aid for paper pulp comprising the polysaccharide of claim 1 .
32. A personal care formulation comprising the polysaccharide of claim 1 .
33. A polysaccharide comprising at least two oxime linkages.
34. A polysaccharide of claim 33 having a weight average molecular weight of at least about 1000 daltons.
35. A polysaccharide of claim 34 having a weight molecular weight of at least about 4000 daltons.
36. A polysaccharide of claim 33 which comprises a plurality of saccharide residues selected from the group consisting of monosaccharide, disaccharide, trisaccharide, and low molecular weight polysaccharide residues.
37. A polysaccharide of claim 36 wherein said monosaccharide residue is derived from galactose.
38. A polysaccharide of claim 36 wherein said disaccharide residue is derived from lactose, melibiose, or galactosyl arabinose.
39. A polysaccharide of claim 36 wherein said low molecular weight polysaccharide residue is derived from degraded galactomannan gum.
40. A polysaccharide of claim 39 wherein said degraded galactomannan gum comprises guar, tara, fenugreek, or locust bean gum.