Synthetic catalysts for carbohydrate processing

Patent metadata

Field	Value
Publication number	US-2022016612-A1
Application number	US-202117368257-A
Country	US
Kind code	A1
Filing date	Jul 6, 2021
Priority date	Jul 6, 2020
Publication date	Jan 20, 2022
Grant date	—

Abstract

The disclosure relates to molecularly-imprinted cross-linked micelles that can selectively hydrolyze carbohydrates.

First claim

We claim:

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 Brønsted 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.

Assignees

• Univ Iowa State Res Found Inc

Inventors

• Zhao Yan

Classifications

• B01J35/23

  in a colloidal state · CPC title

• B01J35/45

  Nanoparticles · CPC title

• B01J31/067 Primary

  Molecularly imprinted polymers (catalytic antibodies C12N9/0002) · CPC title

• C07H1/00 Primary

  Processes for the preparation of sugar derivatives · CPC title

• B01J37/04

  Mixing {(B01J37/0009, B01J37/0018 take precedence)} · CPC title