Nutritional products comprising human milk oligosaccharides and methods for manufacture thereof

Patent metadata

Field	Value
Publication number	US-10499668-B2
Application number	US-201214117424-A
Country	US
Kind code	B2
Filing date	May 10, 2012
Priority date	May 13, 2011
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

A method for the manufacture an infant formula or an infant nutritional product comprising mixture of human milk oligosaccharides is disclosed. The method involves the catalytic hydrogenolysis of compounds of the general formula 1 and 2 with particular oligosaccharide profiles.

First claim

The invention claimed is:

1. A method for manufacturing an infant nutritional product or infant formula comprising a mixture of human milk oligosaccharides (HMOs), the method comprising: subjecting a mixture of at least two compounds selected from the group consisting of compounds of general formula 1 and compounds of general formula 2 to catalytic hydrogenolysis to remove,

wherein R is a group removable by the catalytic hydrogenolysis,
R 1 is independently a fucosyl or an H,
R 2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
R 3 is an H or an N-acetyl-lactosaminyl group
R 4 is independently a sialyl or an H,
and salts thereof,
at least one of R 1 or R 4 is not H in general formula 2, and
a quantity of the mixture of the at least two compounds selected from the group consisting of compounds of general formula 1 and compounds of general formula 2 are selected such that the mixture of human milk oligosaccharides (HMOs) has an oligosaccharide profile that is substantially similar to a milk selected from the group consisting of colostrum breast milk, transitional breast milk and mature breast milk.

2. The method of claim 1 , wherein the catalytic hydrogenolysis is carried out in at least one protic solvent in the presence of a hydrogenolysis catalyst.

3. The method of claim 1 , wherein the at least two compounds are selected from the group consisting of R-glycosides of 2′-fucosyllactose, 3-fucosyllactose, 2′,3-difucosyllactose, 3′-sialyllactose, 6′-sialyllactose, 3′-sialyl-3-fucosyllactose, lacto-N-tetraose, lacto-N-neotetraose, LNFP-I, LNFP-II, LNFP-III, LNFP-V, LST-a, LST-b, LST-c, FLST-a, FLST-b, FLST-c, LNDFH-I, LNDFH-II, LNDFH-III, DS-LNT, FDS-LNT I and FDS-LNT II.

4. The method of claim 1 , wherein the infant nutritional product or infant formula is in a form selected from the group consisting of a liquid, a powder or a solid.

5. The method of claim 1 , comprising adding a component selected from the group consisting of pharmaceutically or nutritionally acceptable carriers, lactose, proteins, and fat to the mixture of human milk oligosaccharides.

6. The method of claim 1 , further comprising adding prebiotics to the mixture of human milk oligosaccharides.

7. The method of claim 1 , wherein the N-acetyl lactosaminyl group comprises a glycosyl residue comprising one or more N-acetyl-lactosaminyl and/or one or more lacto-N-biosyl groups, and at least one N-acetyl-lactosaminyl or lacto-N-biosyl group can be substituted with a sialyl and/or fucosyl residue; and
R 3 is N-acetyl-lactosaminyl group substituted with a glycosyl residue comprising one or more N-acetyl-lactosaminyl and/or one or more lacto-N-biosyl groups, and at least one N-acetyl-lactosaminyl or lacto-N-biosyl group is substituted with a sialyl and/or fucosyl residue.

8. A method for manufacturing an infant nutritional product or infant formula comprising a mixture of human milk oligosaccharides (HMOs), the method comprising: subjecting a mixture of at least two compounds selected from the group consisting of compounds of general formula 1 and general formula 2 to catalytic hydrogenolysis to remove R,

wherein R is a group removable by the catalytic hydrogenolysis,
R 1 is independently a fucosyl or an H,
R 2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
R 3 is an H or an N-acetyl-lactosaminyl group,
R 4 is independently a sialyl or an H,
and salts thereof,
at least one of R 1 or R 4 is not H in general formula 2,
wherein the compounds of general formula 1 are selected from the group consisting of compounds of general formula 1a and compounds of general formula 1b,

R 2a is an N-acetyl-lactosaminyl group substituted with a glycosyl residue comprising one N-acetyl-lactosaminyl and/or one lacto-N-biosyl group; at least one N-acetyl-lactosaminyl or lacto-N-biosyl group is substituted with a sialyl and/or fucosyl residue,
R 3a is an H or an N-acetyl-lactosaminyl group substituted with a lacto-N-biosyl group; at least one N-acetyl-lactosaminyl or lacto-N-biosyl group is substituted with a sialyl and/or fucosyl residue,
R 2b is a lacto-N-biosyl group substituted with sialyl and/or fucosyl residue, and
R 3b is an H or an N-acetyl-lactosaminyl group substituted with one or two N-acetyl-lactosaminyl and/or one lacto-N-biosyl group; at least one N-acetyl-lactosaminyl or lacto-N-biosyl group is substituted with sialyl and/or fucosyl residue, and
a quantity of the mixture of the at least two compounds selected from the group consisting of compounds of general formula 1 and compounds of general formula 2 are selected such that the mixture of human milk oligosaccharides (HMOs) has an oligosaccharide profile that is substantially similar to a milk selected from the group consisting of colostrum breast milk, transitional breast milk and mature breast milk.

9. The method of claim 8 , wherein
the N-acetyl-lactosaminyl group in the glycosyl residue of R 2a in general formula 1a is attached to the another N-acetyl-lactosaminyl group with 1-3 interglycosidic linkage,
the lacto-N-biosyl group in the glycosyl residue of R 2a in general formula 1a is attached to the N-acetyl-lactosaminyl group with 1-3 interglycosidic linkage,
the lacto-N-biosyl group in the glycosyl residue of R 3a in general formula 1a is attached to the N-acetyl-lactosaminyl group with 1-3 interglycosidic linkage,
the N-acetyl-lactosaminyl group in the glycosyl residue of R 3b in general formula 1b is attached to the another N-acetyl-lactosaminyl group with 1-3 or 1-6 interglycosidic linkage, and/or
the lacto-N-biosyl group in the glycosyl residue of R 3b in general formula 1b is attached to the N-acetyl-lactosaminyl group with 1-3 interglycosidic linkage.

10. The method of claim 8 , wherein general formula 1a represents the R-glycosides of lacto-N-neotetraose, para-lacto-N-hexaose, para-lacto-N-neohexaose, lacto-N-neohexaose, para-lacto-N-octaose and lacto-N-neooctaose substituted with one or more sialyl and/or fucosyl residue, and general formula 1b represents the R-glycosides of lacto-N-tetraose, lacto-N-hexaose, lacto-N-octaose, iso-lacto-N-octaose, lacto-N-decaose and lacto-N-neodecaose substituted with one or more sialyl and/or fucosyl residue.

11. A method for manufacturing an infant nutritional product or infant formula comprising a mixture of human milk oligosaccharides (HMOs), the method comprising: subjecting a mixture of at least two compounds selected from the group consisting of compounds of general formula 1 and general formula 2 to catalytic hydrogenolysis to remove R,

wherein R is a group removable by the catalytic hydrogenolysis,
R 1 is independently a fucosyl or an H,
R 2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
R 3 is an H or an N-acetyl-lactosaminyl group,
R 4 is independently a sialyl or an H,
and salts thereof,
at least one of R 1 or R 4 is not H in general formula 2,
the fucosyl residue attached to the N-acetyl-lactosaminyl and/or the lacto-N-biosyl group includes a linkage selected from the group consisting of
the galact

Assignees

• Brassart Dominique
• Dekany Gyula
• Erdmann Peter
• Schwarz Andrea
• Sprenger Norbert
• Nestle Sa

Inventors

• Brassart Dominique
• Dekany Gyula
• Erdmann Peter
• Schwarz Andrea
• Sprenger Norbert

Classifications

• A23L33/125

  containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates (indigestible substances A23L33/21) · CPC title

• A23L5/00 Primary

  Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor · CPC title

• A23L33/40

  Complete food formulations for specific consumer groups or specific purposes, e.g. infant formula · CPC title

• A23L33/00

  Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof · CPC title

• A23L29/30

  containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin (products from apiculture A23L21/20; artificial sweetening agents A23L27/30) · CPC title