Chiral binuclear metal complexes for stereoselective hydrolysis of saccharides and glycosides

Patent metadata

Field	Value
Publication number	US-10870103-B2
Application number	US-201715451478-A
Country	US
Kind code	B2
Filing date	Mar 7, 2017
Priority date	Mar 24, 2016
Publication date	Dec 22, 2020
Grant date	Dec 22, 2020

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.

First claim

What is claimed is:

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:

2. 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.

Assignees

• Univ Arkansas

Inventors

• Striegler Susanne

Classifications

• C07H3/02 Primary

  Monosaccharides · CPC title

• C07C211/36

  containing at least two amino groups bound to the carbon skeleton · CPC title

• C07C215/44

  bound to carbon atoms of the same ring or condensed ring system · CPC title

• C07F1/005

  without C-Metal linkages · CPC title

• C07C2601/14

  The ring being saturated · CPC title