Nutritional products comprising human milk oligosaccharides and methods for manufacture thereof

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,
• R1 is independently a fucosyl or an H,
• R2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
• R3 is an H or an N-acetyl-lactosaminyl group,
• R4 is independently a sialyl or an H,
• and salts thereof,
• at least one of R1 or R4 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,
• R2a 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,
• R3a 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,
• R2b is a lacto-N-biosyl group substituted with sialyl and/or fucosyl residue, and
• R3b 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.

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,
• R1 is independently a fucosyl or an H,
• R2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
• R3 is an H or an N-acetyl-lactosaminyl group,
• R4 is independently a sialyl or an H,
• and salts thereof,
• at least one of R1 or R4 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 galactose of the lacto-N-biosyl group with 1-2 interglycosidic linkage,
• the N-acetyl-glucosamine of the lacto-N-biosyl group with 1-4 interglycosidic linkage, and
• the N-acetyl-glucosamine of the N-acetyl-lactosaminyl group with 1-3 interglycosidic linkage;
• and
• the sialyl residue attached to the N-acetyl-lactosaminyl and/or the lacto-N-biosyl group includes a linkage selected from the group consisting of
• the galactose of the lacto-N-biosyl group with 2-3 interglycosidic linkage,
• the N-acetyl-glucosamine of the lacto-N-biosyl group with 2-6 interglycosidic linkage, and
• the galactose of the N-acetyl-lactosaminyl group with 2-6 interglycosidic linkage, 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.

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 R,
• wherein the R-glycoside is a β-anomer,
• R1 is independently a fucosyl or an H,
• R2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
• R3 is an H or an N-acetyl-lactosaminyl group,
• R4 is independently a sialyl or an H,
• and salts thereof,
• at least one of R1 or R4 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.

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 R,
• wherein R is a benzyl,
• R1 is independently a fucosyl or an H,
• R2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
• R3 is an H or an N-acetyl-lactosaminyl group,
• R4 is independently a sialyl or an H,
• and salts thereof,
• at least one of R1 or R4 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.

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,
• R1 is independently a fucosyl or an H,
• R2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
• R3 is an H or an N-acetyl-lactosaminyl group,
• R4 is independently a sialyl or an H,
• and salts thereof,
• at least one of R1 or R4 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,
• wherein the catalytic hydrogenation leads to human milk oligosaccharides (HMOs) according to general formula 3 and general formula 4
• wherein R1 is independently a fucosyl or an H,
• R2 is an N-acetyl-lactosaminyl group or a lacto-N-biosyl group,
• R3 is an H or an N-acetyl-lactosaminyl group,
• R4 is independently a sialyl or an H,
• and salts thereof, and
• at least one of R1 or R4 is not H in general formula 4.