# US 10,946,032 B2 · Mixtures of HMOs

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- Number: US 10,946,032 B2
- Document ID: US10946032B2
- Status: Granted
- Kind: B2
- Application number: 16/435,949
- Filed: 2019-06-10
- Published: 2019-09-26
- Granted: 2021-03-16
- Earliest claimed: 2014-10-24
- Assignees: Glycom A/S
- Applicants: Glycom A/S
- Inventors: Elise Champion; Bruce McConnell; Gyula Dekany
- Web page: https://patentgrep.com/patent/US10946032B2

## CPC

- A61K 31/702: Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
- A61K 31/7016: Disaccharides, e.g. lactose, lactulose (lactobionic acid A61K31/7032)
- A61K 31/715: Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 37/04: Immunostimulants
- C07H 5/06: Aminosugars
- C12P 19/00: Preparation of compounds containing saccharide radicals (ketoaldonic acids C12P7/58)
- C12P 19/18: produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
- C12P 19/26: Preparation of nitrogen-containing carbohydrates
- C12Y 204/01065: 3-Galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase (2.4.1.65), i.e. alpha-1-3 fucosyltransferase
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12Y: ENZYMES

## Abstract

The invention relates to a mixture of human milk oligosaccharides that consists essentially of: a) a component A which is 3-FL or DFL, a component B which is LNT, LNnT, LNFP-I or 2′-FL, a component C, which is LNFP-II when component B is LNT, or LNFP-III when component B is LNnT, or LNDFH-I when component B is LNFP-I, or DFL when component B is 2′-FL, and a component D, which is lactose when component A is 3-FL, or 2′-FL when component A is DFL, with the proviso that if component B is 2′-FL, then component A is 3-FL; or consists essentially of: b) 3-FL, a component E which is LNT, LNnT or LNFP-I, and a component F, which is LNFP-II when component E is LNT, or LNFP-III when component E is LNnT, or LNDFH-I when component E is LNFP-I, and to processes for producing them and their uses.

## Claims

### Claim 1

A mixture of human milk oligosaccharides (HMOs) consisting essentially of: (a) 3-fucosyllactose, lacto-N-fucopentaose I, lacto-N-difucohexaose I and, optionally, lactose; or (b) difucosyllactose, 2′-fucosyllactose, and (i) lacto-N-tetraose and lacto-N-fucopentaose II, wherein the molar ratio of difucosyllactose to lacto-N-tetraose ranges from 2.5 to 5, (ii) lacto-N-neotetraose and lacto-N-fucopentaose III, wherein the molar ratio of difucosyllactose to lacto-N-neotetraose ranges from 2.5 to 5, or (iii) lacto-N-fucopentaose I and lacto-N-difucohexaose I.

### Claim 2 (depends on 1)

The mixture of HMOs of claim 1, wherein the mixture consists essentially of 3-fucosyllactose, lacto-N-fucopentaose I, lacto-N-difucohexaose I, and, optionally, lactose, and wherein the molar ratio of (3-fucosyllactose+lacto-N-fucopentaose I) to lacto-N-difucohexaose I ranges from 0.8 to 9.50.

### Claim 3 (depends on 2)

The mixture of HMOs of claim 2, wherein the molar ratio of 3-fucosyllactose to lacto-N-difucohexaose I or the molar ratio of lacto-N-fucopentaose I to lacto-N-difucohexaose I is not more than 2.

### Claim 4 (depends on 2)

The mixture of HMOs of claim 2, wherein the molar ratio of 3-fucosyllactose to lacto-N-fucopentaose I ranges from 0.07 to 7.7.

### Claim 5 (depends on 2)

The mixture of HMOs of claim 2, wherein the mixture consists essentially of 3-fucosyllactose, lacto-N-fucopentaose I, lacto-N-difucohexaose I and lactose, and wherein the molar ratio of lactose to lacto-N-difucohexaose I is about 1.

### Claim 6 (depends on 1)

The mixture of HMOs of claim 1, wherein the mixture consists essentially of difucosyllactose, 2′-fucosyllactose, and
(i) lacto-N-tetraose and lacto-N-fucopentaose II,
(ii) lacto-N-neotetraose and lacto-N-fucopentaose III, or
(iii) lacto-N-fucopentaose I and lacto-N-difucohexaose I.

### Claim 7 (depends on 6)

The mixture of HMOs of claim 6, wherein the molar ratio of
(difucosyllactose+lacto-N-tetraose) to lacto-N-fucopentaose II,
(difucosyllactose+lacto-N-neotetraose) to lacto-N-fucopentaose III, or
(difucosyllactose+lacto-N-fucopentaose I) to lacto-N-difucohexaose I
is 0.8-9.50.

### Claim 8 (depends on 6)

The mixture of HMOs of claim 6, wherein the molar ratio of:
lacto-N-fucopentaose II to (difucosyllactose+lacto-N-tetraose),
lacto-N-fucopentaose III to (difucosyllactose+lacto-N-neotetraose), or
lacto-N-difucohexaose I to (difucosyllactose+lacto-N-fucopentaose I)
is at least 0.1.

### Claim 9

A mixture of human milk oligosaccharides (HMOs) consisting essentially of 3-fucosyllactose and:
(a) lacto-N-tetraose, lacto-N-fucopentaose II and, optionally, lactose;
(b) lacto-N-neotetraose, lacto-N-fucopentaose III and, optionally, lactose; or
(c) 2′-fucosyllactose, difucosyllactose and lactose;
wherein the mixture is produced by a process comprising reacting 3-fucosyllactose and the lacto-N-tetraose, lacto-N-neotetraose, or 2′-fucosyllactose in a molar ratio of 0.2-5 in the presence of an α1-3/4 transfucosidase, and then removing the α1-3/4 transfucosidase and optionally the lactose from the reaction mixture, wherein the reaction has a conversion rate of at least 35%.

### Claim 10 (depends on 9)

The mixture of HMOs of claim 9, wherein the mixture consists essentially of 3-fucosyllactose and:
(a) lacto-N-tetraose and lacto-N-fucopentaose II, or
(b) lacto-N-neotetraose and lacto-N-fucopentaose III.

### Claim 11 (depends on 10)

The mixture of HMOs of claim 10, wherein the molar ratio of:
(3-fucosyllactose+lacto-N-tetraose) to lacto-N-fucopentaose II, or
(3-fucosyllactose+lacto-N-neotetraose) to lacto-N-fucopentaose III
is 0.8-9.50.

### Claim 12 (depends on 11)

The mixture of HMOs of claim 11, wherein one of the molar ratios of:
3-fucosyllactose to lacto-N-fucopentaose II and lacto-N-tetraose to lacto-N-fucopentaose II, or
3-fucosyllactose to lacto-N-fucopentaose III and lacto-N-neotetraose to lacto-N-fucopentaose III
is not more than 2.

### Claim 13 (depends on 10)

The mixture of HMOs of claim 10, wherein the molar ratio of the
lacto-N-fucopentaose II to (3-fucosyllactose+lacto-N-tetraose), or
lacto-N-fucopentaose III to (3-fucosyllactose+lacto-N-neotetraose)
is at least 0.1.

### Claim 14 (depends on 10)

The mixture of HMOs of claim 10, wherein the molar ratio of 3-fucosyllactose to lacto-N-tetraose or lacto-N-neotetraose ranges from 0.05 to 21.

### Claim 15 (depends on 9)

The mixture of HMOs of claim 9, wherein the mixture consists essentially of 3-fucosyllactose, lactose and:
(i) lacto-N-tetraose and lacto-N-fucopentaose II,
(ii) lacto-N-neotetraose and lacto-N-fucopentaose III, or
(iii) 2′-fucosyllactose and difucosyllactose.

### Claim 16 (depends on 15)

The mixture of HMOs of claim 15, wherein the molar ratio of
(3-fucosyllactose+lacto-N-tetraose) to lacto-N-fucopentaose II,
(3-fucosyllactose+lacto-N-neotetraose) to lacto-N-fucopentaose III, or
(3-fucosyllactose+2′-fucosyllactose) to difucosyllactose
ranges from 0.8 to 9.50; and wherein the molar ratio of lactose to lacto-N-fucopentaose II, lacto-N-fucopentaose III, or difucosyllatose is about 1.

### Claim 17 (depends on 16)

The mixture of HMOs of claim 16, wherein the molar ratio of 3-fucosyllactose to lacto-N-fucopentaose II, lacto-N-fucopentaose III or difucosyllatose ranges from 0.07 to 7.7.

### Claim 18 (depends on 16)

The mixture of HMOs of claim 16, wherein the molar ratio of 3-fucosyllactose to lactose or the molar ratio of
lacto-N-tetraose to lacto-N-fucopentaose II,
lacto-N-neotetraose to lacto-N-fucopentaose III, or
2′-fucosyllactose and difucosyllactose
is not more than 2.

### Claim 19 (depends on 1)

A method of preventing or treating bacterial infections in a human, the method comprising administering to the human a composition comprising a mixture of HMOs of claim 1.

### Claim 20 (depends on 9)

A method of preventing or treating bacterial infections in a human, the method comprising administering to the human a composition comprising a mixture of HMOs of claim 9.