IP Library Granted Patent US 10,314,852
Granted Patent B2
US 10,314,852 · App. 15/521,582 · Granted Jun 11, 2019

Mixtures of HMOs

Inventors: Elise Champion (Toulouse, FR); Bruce McConnell (La Tour de Peliz, CH); Gyula Dekany (Sinnamon Park, AU)
Assignee: GLYCOM A/S
A61K31/702A61K31/7016A61K31/715C07H5/06C12P19/18C12P19/26C12Y204/01065
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Quick Facts
Patent No.
US 10,314,852
App. No.
15/521,582
Granted
Jun 11, 2019
Kind
B2
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 (34)

1. A process for obtaining the mixture of human milk oligosaccharides (HMOs) consisting essentially of components A, B, C, and D:

wherein

the component A is 3-fucosyllactose or difucosyllactose;

the component B is selected from the group consisting of lacto-N-tetraose, lacto-N-neotetraose, lacto-N-fucopentaose I, and 2′-fucosyllactose;

the component C is

lacto-N-fucopentaose II when the component B is lacto-N-tetraose,

lacto-N-fucopentaose III when the component B is lacto-N-neotetraose,

lacto-N-difucohexaose I when the component B is lacto-N-fucopentaose I, or

difucosyllactose when the component B is 2′-fucosyllactose; and

the component D is

lactose when the component A is 3-fucosyllactose, or

2′-fucosyllactose when the component A is difucosyllactose,

wherein the component A is 3-fucosyllactose when the component B is 2′-fucosyllactose; wherein the process comprises reacting the component A and the component B in the presence of an α1-3/4 transfucosidase to produce a reaction mixture, and then removing the α1-3/4 transfucosidase from the reaction mixture; and

wherein either

the component A is difucosyllactose and the process comprises reacting difucosyllactose and the component B in a molar ratio of 0.2-5 in the presence of an α1-3/4 transfucosidase, wherein the reaction has a conversion rate of at least 10%; or

the component A is 3-fucosyllactose, and the process comprises reacting 3-fucosyllactose and the component B in a molar ratio of 0.2-5 in the presence of an α1-3/4 transfucosidase, wherein the reaction has a conversion rate of at least 35%.

2. The process according to claim 1 , wherein the process is used to obtain the mixture wherein the component B is lacto-N-tetraose or lacto-N-neotetraose, and the molar ratio of (a) 3-fucosyllactose to the component C or (b) the component B to the component C is not more than 2.

3. The process according to claim 1 , wherein the process comprises reacting 3-fucosyllactose and the component B in a molar ratio of 0.33-3 in the presence of an α1-3/4 transfucosidase.

4. A process for obtaining a mixture of human milk oligosaccharides (HMOs) consisting essentially of:

3-fucosyllactose;

a component B selected from the group consisting of lacto-N-tetraose, lacto-N-neotetraose, lacto-N-fucopentaose I and 2′-fucosyllactose; and

a component C which is

lacto-N-fucopentaose II when the component B is lacto-N-tetraose,

lacto-N-fucopentaose III when the component B is lacto-N-neotetraose,

lacto-N-difucohexaose I when the component B lacto-N-fucopentaose I, or

difucosyllactose when the component B is 2′-fucosyllactose; and

comprising reacting 3-fucosyllactose and the component B in the presence of an α1-3/4 transfucosidase to produce a reaction mixture, and then removing lactose and the α1-3/4 transfucosidase from the reaction mixture;

wherein the process comprises reacting 3-fucosyllactose and the component B in a molar ratio of 0.2-5 in the presence of an α1-3/4 transfucosidase, wherein the reaction has a conversion rate of at least 35%.

5. The process according to claim 4 , wherein the mixture of HMOs consists essentially of:

3-fucosyllactose;

a component B selected from the group consisting of lacto-N-tetraose, lacto-N-neotetraose, and lacto-N-fucopentaose I; and a component C which is

lacto-N-fucopentaose II when the component E is lacto-N-tetraose,

lacto-N-fucopentaose III when the component E is lacto-N-neotetraose, or

lacto-N-difucohexaose I when the component E is lacto-N-fucopentaose I.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 25, 2018
From: CHAMPION, ELISE; MCCONNELL, BRUCE; DEKANY, GYULA
To: GLYCOM A/S
Reel/Frame 045905/0585 →
Priority Claims (6)
EP 14190374 · Oct 24, 2014 · regional
EP 15155450 · Feb 17, 2015 · regional
EP 15155454 · Feb 17, 2015 · regional
EP 15155457 · Feb 17, 2015 · regional
EP 15163044 · Apr 9, 2015 · regional
EP 15163047 · Apr 9, 2015 · regional
Continuity (1)
Related Publication 20170312298A1 · Nov 2, 2017