# US 10,870,103 B2 · Chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides

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- Number: US 10,870,103 B2
- Document ID: US10870103B2
- Status: Granted
- Kind: B2
- Application number: 15/451,478
- Filed: 2017-03-07
- Published: 2017-09-28
- Granted: 2020-12-22
- Earliest claimed: 2016-03-24
- Assignees: Board of Trustees of the University of Arkansas
- Applicants: Board of Trustees of the University of Arkansas
- Inventors: Susanne Striegler
- Web page: https://patentgrep.com/patent/US10870103B2

## CPC

- B01J 31/2239: {Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands}
- B01J 31/2243: {At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand}
- C07C 211/36: containing at least two amino groups bound to the carbon skeleton
- C07C 215/44: bound to carbon atoms of the same ring or condensed ring system
- C07F 1/005: {without C-Metal linkages}
- C07H 1/00: Processes for the preparation of sugar derivatives
- C07H 3/02: Monosaccharides
- B01J 2531/0208: Bimetallic complexes, i.e. comprising one or more units of two metals, with metal-metal bonds but no all-metal (M)n rings, e.g. Cr2(OAc)4
- B01J 2531/0238: Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J 2531/16: Copper
- C07B 2200/07: Optical isomers
- C07C 2601/14: The ring being saturated
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Disclosed herein is a class of chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides, and more particular chiral binuclear transition metal complex catalysts that discriminate epimeric glycosides and α- and β-glycosidic bonds of saccharides in aqueous solutions at near physiological pHs. The chiral binuclear metal complexes include a Schiff-base-type ligand derived from a chiral diamino building block, and a binuclear transition metal core, each which can be varied for selectivity. The metal core is a Lewis-acidic metal ion, such as copper, zinc, lanthanum, iron and nickel. The Schiff-base may be a reduced or non-reduced Schiff-base derived from aliphatic linear, aliphatic cyclic diamino alcohols or aromatic aldehydes. The ligand can be a penta- or heptadentate ligand derived from pyridinecarbaldehydes, benzaldehydes, linear or cyclic diamines or diamino alcohols.

## Claims

### Claim 1

A method of hydrolysis of saccharides and glycosides, said method comprising the steps of:
discriminating α glycosidic bonds of saccharides in aqueous solutions using an enantiopure asymmetric chiral binuclear transition metal (II) complex wherein the formula of said enantiopure asymmetric chiral binuclear transition metal (II) complex is:

### Claim 2 (depends on 1)

The method of claim 1 further comprises the step of discriminating said α-glycosidic bonds of saccharides in aqueous solutions at a pH range from 7.45 to 7.55 using said chiral binuclear transition metal (II) complex.