Synthetic catalysts for carbohydrate processing

Patent metadata

Field	Value
Publication number	US-12420272-B2
Application number	US-202418636070-A
Country	US
Kind code	B2
Filing date	Apr 15, 2024
Priority date	Jul 6, 2020
Publication date	Sep 23, 2025
Grant date	Sep 23, 2025

Abstract

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

First claim

I claim:

1. A molecularly-imprinted cross-linked micelle selective for a glycan, the micelle comprising:
an imprint of a functional or structural analogue of the glycan; and
a binding unit and an acid unit, wherein the binding unit is bindable to the glycan, the acid unit is proximal to a glycosidic bond of the glycan during binding of the glycan to the binding unit, the acid unit is obtained from H 2 N-(1,4-phenyl)-COOH, H 2 N—(CH 2 ) n —COOH, H 2 N—(CH 2 ) n —PO 3 H 2 , or H 2 N—(CH 2 ) n —SO 3 H, and wherein n is 1 to 6.

2. The micelle of claim 1 , wherein the functional or structural analogue of the glycan is:

3. The micelle of claim 1 , wherein the functional or structural analogue of the glycan is:

4. The micelle of claim 1 , wherein the functional or structural analogue of the glycan is:

5. The micelle of claim 1 , wherein the functional or structural analogue of the glycan is:

6. The micelle of claim 1 , wherein the acid unit is obtained from H 2 N-(1,4-phenyl)-COOH.

7. The micelle of claim 1 , wherein the acid unit is obtained from H 2 N—(CH 2 ) n —COOH, wherein n is 1 to 6.

8. The micelle of claim 1 , wherein the acid unit is obtained from H 2 N—(CH 2 ) n —PO 3 H 2 , wherein n is 1 to 6.

9. The micelle of claim 8 , wherein n is 3.

10. The micelle of claim 1 , wherein the acid unit is obtained from H 2 N—(CH 2 ) n —SO 3 H, wherein n is 1 to 6.

11. The micelle of claim 10 , wherein n is 3.

12. The micelle of claim 1 , wherein the micelle comprises surfactants comprising one or more polymerizable vinyl groups that are polymerizable by free radical polymerization.

13. The micelle of claim 1 , wherein the micelle comprises a surface and a core and is cross-linked on the surface by covalent bonds and 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, wherein the acid unit is obtained from H 2 N-(1,4-phenyl)-COOH, H 2 N—(CH 2 ) n —COOH, H 2 N—(CH 2 ) n —PO 3 H 2 , or H 2 N—(CH 2 ) n —SO 3 H, and wherein n is 1 to 6.

17. The method of claim 16 , wherein the functional or structural analogue of the glycan has the structure:

18. A method of hydrolyzing an oligosaccharide or polysaccharide, comprising contacting the oligosaccharide or polysaccharide with the micelle of claim 1 .

19. The method of claim 18 , wherein the oligosaccharide or polysaccharide is cellulose.

20. A molecularly-imprinted cross-linked micelle selective for a glycan, the micelle comprising:
an imprint of a functional or structural analogue of the glycan; and
a binding unit and an acid unit, wherein the binding unit is bindable to the glycan, the acid unit is proximal to a glycosidic bond of the glycan during binding of the glycan to the binding unit, and wherein the functional or structural analogue of the glycan has the structure:

Assignees

• Univ Iowa State Res Found Inc

Inventors

• Zhao Yan

Classifications

• B01J35/23

  in a colloidal state · CPC title

• B01J35/45

  Nanoparticles · CPC title

• C13K1/02

  obtained by saccharification of cellulosic materials (manufacture of fodder A23K10/32) · CPC title

• B01J37/04

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

• B01J31/067 Primary

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