Oligosaccharide compositions and methods for producing thereof
Described herein are methods for the production of oligosaccharides, including functionalized oligosaccharides, from one or more sugars, such as one or more monosaccharides, using polymeric and solid-supported catalysts containing acidic and ionic groups. Also provided are the oligosaccharide compositions, including functionalized oligosaccharide compositions, obtained using the methods.
1. An oligosaccharide composition prepared according to a method comprising condensation polymerization of one or more sugars to produce the oligosaccharide composition;
the oligosaccharide composition comprising:
monosaccharide monomers connected by glycosidic bonds;
wherein:
each of the monosaccharide monomers is selected from the group consisting of C5 monosaccharides and C6 monosaccharides; at least 15% of the oligosaccharide composition has a degree of polymerization (DP) of at least four; 5 to 25% of the oligosaccharide composition has a degree of polymerization (DP) of three; and 5 to 30% of the oligosaccharide composition has a degree of polymerization (DP) of two;
the mean DP of the oligosaccharide composition is 10-15; and
at least a portion of the glycosidic bonds in the oligosaccharide composition comprises β-1,2 bonds and α-1,3 bonds.
2. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are glucose, galactose, xylose, arabinose, fructose, mannose, ribose, allose, fucose, or rhamnose.
3. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are connected by glycosidic bonds to form oligomer backbones, and wherein the oligomer backbones are optionally substituted with one or more pendant functional groups, wherein the pendant functional groups are carboxylic acids, sugar alcohols, amino acids, amino sugars, alcohols, sulfate, or phosphate.
4. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are connected by glycosidic bonds to form oligomer backbones, and wherein at least a portion of the oligosaccharide composition further comprises one or more bridging functional groups, wherein:
each bridging functional group connects one of the oligomer backbones to an additional monosaccharide monomer, a disaccharide, or an additional oligomer backbone; and
the one or more bridging functional groups are polyols, polycarboxylic acids, or amino acids.
5. The oligosaccharide composition of claim 4 , wherein each additional oligomer backbone is optionally substituted with one or more pendant functional groups, wherein the pendant functional groups are carboxylic acids, sugar alcohols, amino acids, amino sugars, alcohols, sulfate, or phosphate.
6. The oligosaccharide composition of claim 3 , wherein the one or more pendant functional groups are glucosamine, galactosamine, citric acid, succinic acid, glutamic acid, aspartic acid, glucuronic acid, butyric acid, itaconic acid, malic acid, maleic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, adipic acid, isobutyric acid, formic acid, levulinic acid, valeric acid, isovaleric acid, sorbitol, xylitol, arabitol, glycerol, erythritol, mannitol, galacitol, fucitol, iditol, inositol, volemitol, lacitol, ethanol, propanol, butanol, pentanol, hexanol, propanediol, butanediol, pentanediol, sulfate, or phosphate.
7. The oligosaccharide composition of claim 4 , wherein the one or more bridging functional groups are glucosamine, galactosamine, lactic acid, acetic acid, citric acid, pyruvic acid, succinic acid, glutamic acid, aspartic acid, glucuronic acid, itaconic acid, malic acid, maleic acid, adipic acid, sorbitol, xylitol, arabitol, glycerol, erythritol, mannitol, galacitol, fucitol, iditol, inositol, volemitol, lacitol, propanediol, butanediol, pentanediol, sulfate, or phosphate.
8. The oligosaccharide composition of claim 1 , wherein greater than 50% of the oligosaccharide composition has a DP of at least four.
9. The oligosaccharide composition of claim 1 , wherein at least 90% of the oligosaccharide composition comprises a mixture of non-alpha-1,4-bonds.
10. The oligosaccharide composition of claim 1 , wherein at least 99% of the oligosaccharide composition comprises a mixture of non-alpha-1,4-bonds.
11. The oligosaccharide composition of claim 1 , wherein the hygroscopicity of the oligosaccharide composition is between 5% moisture content and 15% moisture content at a water activity of at least 0.6.
12. The oligosaccharide composition of claim 1 , wherein the oligosaccharide composition is soluble in water up to a maximum concentration of at least 50 Brix.
13. The oligosaccharide composition of claim 1 , wherein the oligosaccharide composition is soluble in water up to a maximum concentration of at least 70 Brix.
14. The oligosaccharide composition of claim 1 , wherein the oligosaccharide composition is a syrup.
15. The oligosaccharide composition of claim 1 , wherein the oligosaccharide composition is a powder.
16. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are C6 monosaccharides.
17. The oligosaccharide composition of claim 1 , wherein the glycosidic bonds in said oligosaccharide composition are α-1,4 bonds, α-1,2 bonds, β-1,2 bonds, α-1,3 bonds, β-1,3 bonds, β-1,4 bonds, α-1,6 bonds, or β-1,6 bonds.
18. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are C5 monosaccharides.
19. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are arabinose and galactose.
20. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are glucose.
21. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are galactose and glucose.
22. The oligosaccharide composition of claim 1 , wherein the monosaccharide monomers are galactose.
23. The oligosaccharide composition of claim 1 , wherein the oligosaccharide composition comprises non-carbohydrate by-products.
24. The oligosaccharide composition of claim 23 , wherein the non-carbohydrate by-products comprise polyfuranics or solid humins.