Synthesis of oligosaccharides as prebiotics from simple sugars and polysaccharides in concentrated acids

Patent metadata

Field	Value
Publication number	US-12570805-B2
Application number	US-202217832490-A
Country	US
Kind code	B2
Filing date	Jun 3, 2022
Priority date	Jun 4, 2021
Publication date	Mar 10, 2026
Grant date	Mar 10, 2026

Abstract

Provided herein are methods for preparing a product including predominantly prebiotic oligosaccharides by non-enzymatic methods of glycosylation of monosaccharides, disaccharides, and/or polysaccharides. The methods may include mixing one or more types of monosaccharides, disaccharides, and/or polysaccharides with an effective amount of a dehydrating acid at a temperature sufficient to form a product including predominantly prebiotic oligosaccharides.

First claim

The invention claimed is:

1 . A method comprising reacting a mixture comprising about 1 wt % to about 90 wt % of one or more types of monosaccharides, disaccharides, and/or polysaccharides and about 64 to about 98 wt % of dehydrating acid to provide a product predominantly comprising prebiotic oligosaccharides; wherein the mixture is reacted at a temperature of about 10° C. to about 160° C.

2 . The method of claim 1 , wherein the one or more types of monosaccharides, disaccharides, and/or polysaccharides thereof is reacted in a solution comprising a dehydrating acid selected from sulfuric and phosphoric acid.

3 . The method of claim 2 , wherein the solution comprises about 64 to about 92 wt % sulfuric acid.

4 . The method of claim 2 , wherein the solution comprises about 70 to about 90 wt % phosphoric acid.

5 . The method of claim 1 , wherein the dehydrating acid is H 2 SO 4 or H 3 PO 4.

6 . The method of claim 1 , wherein the temperature is about 50° C. to about 90° C.

7 . The method of claim 1 , wherein the temperature is about 25° C. to about 70° C.

8 . The method of claim 1 , wherein the mixtures comprises glucose, fructose, galactose, xylose, levoglucosan, mannose, arabinose, sucrose, lactose, maltose, isomaltose, gentiobiose, cellobiose, trehalose, apiose, rhamnose, hydrolyzed starch, hydrolyzed cellulose, hydrolyzed lignocellulosic biomass, hydrolyzed dextrin, hydrolyzed dextran, or a combination of two or more thereof.

9 . The method of claim 1 , wherein the mixture comprises about 1 to about 50 wt % of the one or more monosaccharides and/or disaccharides.

10 . The method of claim 1 , wherein the mixture comprises about 20 to about 70 wt % of the one or more monosaccharides and/or disaccharides.

11 . The method of claim 1 , wherein the one or more monosaccharides and/or disaccharides and the acid are reacted for 1 minute to 60 minutes.

12 . The method of claim 1 , wherein the prebiotic oligosaccharides of the product are selected from the group consisting of glucooligosaccharides (GlOS or GlcOS), fructooligosaccharides (FOS), galactooligosaccharides (GaOS or GOS), xylooligosaccharides (XOS), maltooligosaccharides, isomaltooligosaccharides (IMO), and mannooligosaccharides, cellooligosaccharides, pecticoligosaccharides (POS) and combinations of any two or more thereof.

13 . The method of claim 1 , wherein the prebiotic oligosaccharides of the product contain one or more glycosidic bonds selected from the group consisting of (α, α)-1,1; (α, β)-1,1; (β, β)-1,1; α/⊕-1,2; α/β-1,3; α/β-1,4; and α/β-1,6.

14 . The method of claim 1 , wherein the prebiotic oligosaccharides of the product have a degree of polymerization of 2 to 10.

15 . The method of claim 14 , wherein the mixture is reacted at a temperature of 50° C. to 70° C. and wherein the prebiotic oligosaccharides of the product have a degree of polymerization of about 3.

16 . The method of claim 1 , wherein the mixture is reacted at a temperature of 90° C. and wherein the prebiotic oligosaccharides of the product have a degree of polymerization of about 4 to 7.

17 . The method of claim 1 , further comprising purifying the product.

18 . The method of claim 17 , wherein the product is purified using nanofiltration, adsorption chromatography on charcoal, ion-exchange chromatography, or low-pressure gel permeation chromatography.

19 . The method of claim 1 , wherein the one or more polysaccharides comprise cellulose, hemicellulose, corn stover, or a combination of two or more thereof.

20 . The method of claim 1 , wherein the mixtures comprises glucose, fructose, galactose, xylose, levoglucosan, mannose, arabinose, sucrose, lactose, maltose, isomaltose, gentiobiose, cellobiose, trehalose, apiose, rhamnose, or a combination of two or more thereof.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Pan Xuejun
• Zeng Meijun
• Li Ning

Classifications

• C07H1/08 Primary

  from natural products · CPC title

• C07H3/06

  Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages · CPC title

• C08H8/00 Primary

  Macromolecular compounds derived from lignocellulosic materials {(pretreatment thereof B27N)} · CPC title