# US 8,771,780 B2 · Oligosaccharide ingredient

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- Number: US 8,771,780 B2
- Document ID: US8771780B2
- Status: Granted
- Kind: B2
- Application number: 13/203,867
- Filed: 2009-03-04
- Published: 2012-02-23
- Granted: 2014-07-08
- Earliest claimed: 2009-03-04
- Assignees: Nestec S.A.
- Applicants: Norbert Sprenger; Rafael Berrocal; Marie-Claire Fichot
- Inventors: Norbert Sprenger; Rafael Berrocal; Marie-Claire Fichot
- Web page: https://patentgrep.com/patent/US8771780B2

## CPC

- C07H 3/04: Disaccharides
- A23L 33/10: using additives (addition of substantially indigestible substances A23L33/21)
- A23L 33/40: {Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula}
- C07H 3/06: Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

An oligosaccharide ingredient comprising glycosylated amino acids and peptides of the general formula RnSacm where R is an amino acid residue, Sac is a monosaccharide selected from the group comprising N-acetyl-neuraminic acid, N-acetyl galactosamine and galactose, n has a value between 1 and 10 with the proviso that if n has the value 1 R is a threonine residue or a serine residue and if n has a value between 2 and 10 the peptide contains at least one threonine or serine residue, m has a value between 2 and 4 and at least 20 mol % of the ingredient is N-acetyl-neuraminic acid.

## Claims

### Claim 1

An oligosaccharide ingredient comprising glycosylated amino acids and peptides of a general formula RnSacm where R is an amino acid residue, Sac is a monosaccharide selected from the group comprising N-acetyl-neuraminic acid, N-acetyl galactosamine and galactose, n has a value between 1 and 10 with the proviso that if n is 1 R is selected from the group consisting of a threonine residue and a serine residue and if n has a value between 2 and 10 the peptide contains at least one residue selected from the group consisting of threonine and serine residue, m has a value between 2 and 4, the oligosaccharide ingredient comprising 10 to 25 mol % N-acetyl galactosamine, 10 to 25 mol % galactose, 20 to 50 mol % N-acetyl-neuraminic acid and 15 to 50 mol % threonine or serine or a mixture thereof, the oligosaccharide ingredient comprising a glycosylated amino acid or peptide selected from the group consisting of NeuAc-α-2,3-Gal-β-1,3-(NeuAc-α-2,6-)-GalNAc-Rn, NeuAc-α-2,3-Gal-β-1,3-GalNAc-Rn, Gal-β-1,3-(NeuAc-α-2,6-)-GalNAc-Rn, and Gal-β-1,3-GalNAc-Rn.

### Claim 2 (depends on 1)

An oligosaccharide ingredient as claimed in claim 1 wherein n has a value between 1 and 3.

### Claim 3 (depends on 1)

An oligosaccharide ingredient as claimed in claim 1 wherein m has a value of 2 or 3.

### Claim 4

A food product comprising an oligosaccharide ingredient comprising glycosylated amino acids and peptides of a general formula RnSacm where R is an amino acid residue, Sac is a monosaccharide selected from the group comprising N-acetyl-neuraminic acid, N-acetyl galactosamine and galactose, n has a value between 1 and 10 with the proviso that if n is 1 R is selected from the group consisting of a threonine residue and a serine residue and if n has a value between 2 and 10 the peptide contains at least one residue selected from the group consisting of threonine and serine residue, m has a value between 2 and 4 and at least 20 mol % of the ingredient is N-acetyl-neuraminic acid, the oligosaccharide ingredient comprising 10 to 25 mol % N-acetyl galactosamine, 10 to 25 mol % galactose, 20 to 50 mol % N-acetyl-neuraminic acid and 15 to 50 mol % threonine or serine or a mixture thereof, the oligosaccharide ingredient comprising a glycosylated amino acid or peptide selected from the group consisting of NeuAc-α-2,3-Gal-β-1,3-(NeuAc-α-2,6-)-GalNAc-Rn, NeuAc-α-2,3-Gal-β-1,3-GalNAc-Rn, Gal-β-1,3-(NeuAc-α-2,6-)-GalNAc-Rn, and Gal-β-1,3-GalNAc-Rn.

### Claim 5 (depends on 4)

A food product as claimed in claim 4 which is an infant formula.

### Claim 6 (depends on 4)

A food product as claimed in claim 4 comprising from 0.2 to 4.0% by weight of the oligosaccharide ingredient.

### Claim 7 (depends on 1)

An oligosaccharide ingredient as claimed in claim 1 wherein the oligosaccharide ingredient has at least one glycosylated amino acid selected from the group consisting of NeuAc-α-2,3-Gal-β-1,3-(NeuAc-α-2,6-)-GalNAc-Rn and Gal-β-1,3-(NeuAc-α-2,6-)-GalNAc-Rn.

### Claim 8 (depends on 4)

A food product as claimed in claim 4, wherein the oligosaccharide ingredient comprises at least one glycosylated amino acid selected from the group consisting of NeuAc-α-2,3-Gal-β-1,3-(NeuAc-α-2,6-)-GalNAc-Rn and Gal-β-1,3-(NeuAc-α-2,6-)-GalNAc-Rn.