Synthetic catalysts for carbohydrate processing
View Patent ↗The disclosure relates to molecularly-imprinted cross-linked micelles that can selectively hydrolyze carbohydrates.
1. A molecularly-imprinted cross-linked micelle selective for a glycan, the micelle comprising:
an imprint of the functional or structural analogue of a glycan;
a binding unit and an acid unit, wherein the binding unit is bindable to the glycan;
and the acid unit is proximal to a glycosidic bond of the glycan during binding of the glycan to the binding unit.
2. The micelle of claim 1 , wherein the micelle is obtained from the functional or structural analogue of a glycan as a template.
3. The micelle of claim 1 , wherein the functional or structural analogue of the glycan is a monosaccharide.
4. The micelle of claim 1 , wherein the functional or structural analogue of the glycan is an oligosaccharide or polysaccharide.
5. The micelle of claim 1 , wherein the functional or structural analogue of the glycan is glucose, maltose, or maltotriose.
6. The micelle of claim 1 , wherein the acid unit is a double acid.
7. The micelle of claim 1 , wherein the acid unit is a Br∅nsted acid.
8. The micelle of claim 7 , wherein the acidic unit is a carboxylic acid, sulfonic acid, or a phosphonic acid.
9. The micelle of claim 1 , wherein the acid unit is a Lewis acid.
10. The micelle of claim 1 , wherein the micelle is obtained from cross-linkable surfactants containing one or more functional groups that are polymerizable and cross-linkable.
11. The micelle of claim 1 , wherein the micelle comprises surfactants comprising one or more polymerizable vinyl groups that are polymerizable by free radical polymerization.
12. The micelle of claim 1 , wherein the micelle comprises a surface and a core and is cross-linked on the surface by covalent bonds.
13. The micelle of claim 1 , wherein the micelle is cross-linked in the core by covalent bonds.
14. The micelle of claim 1 , wherein the binding unit comprises a boroxole, a boronic acid, or an amide group.
15. A material comprising the micelle of claim 1 , wherein the micelle is covalently or non-covalently bonded to a solid support.
16. A method of making the molecularly imprinted micelle of claim 1 comprising:
cross-linking the surface of a micelle comprising a cross-linkable surfactant, a functional or structural analogue of a glycan, a functional monomer that binds the glycan or analogue by covalent or noncovalent bonds, a free radical cross-linker, and a free radical initiator;
cross-linking the surface of the micelle;
cross-linking the core of the micelle;
removing a portion or the entire functional or structural analogue of the glycan to create an imprinted site; and
attaching an acid unit to the imprinted site by covalent bond formation, metal-ligand complexation, or non-covalent interactions.
17. A method of hydrolyzing an oligosaccharide or polysaccharide, comprising contacting the oligosaccharide or polysaccharide with the micelle of claim 1 .
18. The method of claim 17 , wherein during the contacting of the oligosaccharide or polysaccharide with the micelle of claim 1 , the oligosaccharide or polysaccharide is dissolved and/or suspended in an aqueous buffer, a weak acid, ionic liquids, or in a mixture of ionic liquids and organic solvent.
19. The method of claim 17 , wherein during the contacting of the oligosaccharide or polysaccharide with the micelle of claim 1 , the oligosaccharide or polysaccharide is dissolved and/or suspended in water.
20. The method of claim 17 , wherein the oligosaccharide or polysaccharide is cellulose.