Abstract: A mixture of human milk oligosaccharides that consists essentially of 6?-SL, LNnT and LSTc, made by treating 6?-SL and LNnT in the presence of an ?2,6-transsialidase.
Type:
Grant
Filed:
June 9, 2016
Date of Patent:
June 30, 2020
Assignee:
GLYCOM A/S
Inventors:
Elise Champion, Bruce McConnell, Gyula Dekany
Abstract: The invention relates to crystalline polymorphs of lacto-N-tetraose (LNT) and methods for making the same for use in pharmaceutical compositions, nutritional formulations and food supplements.
Type:
Grant
Filed:
December 16, 2016
Date of Patent:
June 30, 2020
Assignee:
GLYCOM A/S
Inventors:
Martin Matwiejuk, Pierre Chassagne, Markus Jondelius Hederos
Abstract: The invention relates to a method for selective crystallization of 2?-FL from an aqueous solution comprising 2?-FL and one or more other fucosylated carbohydrates by adding acetic acid to the solution.
Type:
Grant
Filed:
December 16, 2015
Date of Patent:
June 9, 2020
Assignee:
GLYCOM A/S
Inventors:
Gyula Dekany, Györgyi Osztrovszky, Martin Matwiejuk, Pierre Chassagne, Markus Jondelius Hederos
Abstract: A mixture of human milk oligosaccharides that consists essentially of 3?-O-sialyllactose, a component A which is either 3-O-fucosyllactose or lacto-N-tetraose, a component B which is 3-O-fucosyl-3?-O-sialyllactose when component A is 3-O-fucosyllactose and sialyllacto-N-tetraose a, when component A is lacto-N-tetraose and optionally lactose as a fourth component. The mixtures are made by treating 3?-O-sialyllactose and component A with an ?2,3-transsialidase. The mixtures are for use in anti-bacterial and anti-viral compositions, and for promoting the development of Bifidobacterium and Barnesiella.
Type:
Grant
Filed:
March 31, 2016
Date of Patent:
March 17, 2020
Assignee:
GLYCOM A/S
Inventors:
Elise Champion, Bruce McConnell, Gyula Dekany
Abstract: A composition and method for using it to prevent and/or relieve symptoms of acute respiratory tract infections, particularly bronchitis, in immune-compromised persons, particularly adults. The composition contains 2?-fucosyllactose and lacto-N-neotetraose and/or lacto-N-tetraose.
Type:
Grant
Filed:
March 4, 2016
Date of Patent:
November 12, 2019
Assignee:
Glycom A/S
Inventors:
Bruce McConnell, Louise Kristine Vigsnæs
Abstract: The invention provides engineered enzymes of transsialidase and/or sialyl transferase activity that have increased regioselectivity and/or increased thermostability.
Type:
Grant
Filed:
June 9, 2016
Date of Patent:
October 1, 2019
Assignee:
GLYCOM A/S
Inventors:
Andreas Vogel, Ramona Schmiedel, Elise Champion, Gyula Dekany
Abstract: Mutated fucosidases are provided demonstrating improved properties in terms of thermal stability and transfucosidase synthetic performance compared with a wild type transfucosidase isolated from Bifidobacterium longum subsp. infantis.
Type:
Grant
Filed:
October 23, 2015
Date of Patent:
September 17, 2019
Assignee:
GLYCOM A/S
Inventors:
Elise Champion, Andreas Vogel, Sebastian Bartsch, Gyula Dekany
Abstract: The application discloses a method for producing an oligosaccharide of at least four monosaccharide units, advantageously an HMO, particularly an HMO of only four monosaccharide units, said method comprising a step of: culturing, in a culture medium containing a fucosylated, sialylated or N-acetyl-glucosaminylated lactose trisaccharide as acceptor, a genetically modified cell having a recombinant gene that encodes an enzyme capable of modifying said acceptor or one of the necessary intermediates in the biosynthetic pathway of the oligosaccharide of at least four monosaccharide units, advantageously an HMO, particularly an HMO of only four monosaccharide units, from said acceptor.
Type:
Grant
Filed:
September 5, 2014
Date of Patent:
July 30, 2019
Assignee:
Glycom A/S
Inventors:
Gyula Dekany, Pauline Peltier-Pain, Dóra Molnár-Gábor, Markus Jondelius Hederos
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.
Type:
Grant
Filed:
October 23, 2015
Date of Patent:
June 11, 2019
Assignee:
GLYCOM A/S
Inventors:
Elise Champion, Bruce McConnell, Gyula Dekany
Abstract: A synthetic mixture of human milk oligosaccharides (HMOs) consisting essentially of lacto-N-neotetraose (LNnT), lacto-N-tetraose (LNT), 2?-fucosyllactose (2?FL), 3?-O-sialyllactose (3?-SL), 6?-O-sialyllactose (6?-SL) either difucosyllactose (DFL) or 3-fucosyllactose (3-FL), preferably DFL, and optionally lactose. Said synthetic composition is useful for: treating or preventing viral and/or bacterial infection in a non-infant human; modulating the microbiota of a non-infant human; and/or improving the cognitive function of a non-infant human and as a pharmaceutical or nutritional composition.
Type:
Application
Filed:
December 15, 2016
Publication date:
December 27, 2018
Applicant:
GLYCOM A/S
Inventors:
Bruce MCCONNELL, Louise Kristine VIGNÆS
Abstract: An achemo-enzymatic synthesis of oligosaccharides of formula 1 is presented wherein R is selected from —OH, —N 3 and —OR 6 wherein R 6 is selected from allyl optionally substituted by one or more methyl, propargyl optionally substituted by one or more methyl, 2-trimethylsilyl-ethyl, —(CH 2) n —NH 2 and —(CH 2) n —N 3 wherein integer n is to 10, preferably 2 or 3, R is selected from sialyl moiety, —SO 3 H and —CH(R)—COOH wherein R is selected from H, alkyl and benzyl, R 2 is selected from H and fucosyl, R 3 is selected from H and sialyl, R 4 is selected from H and fucosyl, provided that at least one of R 3 and R 4 is H, and A is a divalent carbohydrate linker, having important biological activities and significant commercial value for the pharmaceutical and food industry.
Type:
Grant
Filed:
April 11, 2014
Date of Patent:
June 26, 2018
Assignee:
GLYCOM A/S
Inventors:
Pierre Chassagne, Nikolay Khanzhin, Markus Jondelius Hederos, Elise Champion, Martin Matwiejuk, Gyula Dekany
Abstract: A method of diversification of human milk oligosaccharides (HMOs) or precursors thereof, compounds obtainable by the method, and uses and compositions involving such compounds. The method comprises a) providing at least one compound or a mixture of the compounds selected from the group consisting of: optionally sialylated and/or fucosylated lactose derivatives of general formula 2 and salts thereof; b) adding at least one enzyme comprising a transglycosidase activity to the at least one compound or a mixture of compounds provided according to step a); and c) incubating the mixture obtained according to step b).
Type:
Grant
Filed:
May 23, 2016
Date of Patent:
May 8, 2018
Assignee:
GLYCOM A/S
Inventors:
Gyula Dekany, Elise Champion, Markus Jondelius Hederos
Abstract: The present application discloses a method of making a mixture of 2?-FL and DFL in high yield by culturing, with lactose, a genetically modified cell having a recombinant gene that encodes a single fucosyl transferase. The resulting mixture of 2?-FL and DFL can be subjected to hydrolysis initiated by an acid or mediated by a fucosidase to produce fucose in high yields.
Type:
Grant
Filed:
September 5, 2014
Date of Patent:
February 27, 2018
Assignee:
GLYCOM A/S
Inventors:
Gyula Dekany, Pauline Peltier-Pain, Dóra Molnár-Gábor, Markus Hederos
Abstract: The present application discloses a method for enhancing the stability of a human milk oligosaccharide (HMO) or a HMO precursor or a HMO blend when stored for extended periods at temperatures above 25° C. by spray-drying an aqueous solution of the HMO or HMO precursor to remove at least 90% of the water and providing a HMO or a HMO precursor or a HMO blend with a specific glass transition temperature. Also disclosed is a method for removing organic solvent residues from a human milk oligosaccharide (HMO) or a HMO precursor or a HMO blend by spray drying. Also disclosed is a method of enhancing the bioavailability of a human milk oligosaccharide (HMO) or a HMO precursor or a HMO blend by spray drying.
Type:
Grant
Filed:
June 14, 2013
Date of Patent:
February 20, 2018
Assignee:
Glycom A/S
Inventors:
Andreas Schroven, Gyula Dekany, Peter Erdmann, Andrea Schwarz
Abstract: The invention relates to a method for producing a glycoconjugate comprising an oligosaccharide part covalently linked to a non-sugar moiety selected from the group consisting of amino acids, peptides, proteins, lipids, longer alkyl groups, polyethylene glycols, ?,?-unsaturated amido group and polyvinyl alcohols, using a genetically modified cell.
Type:
Grant
Filed:
September 25, 2013
Date of Patent:
November 14, 2017
Assignee:
Glycom A/S
Inventors:
Pauline Peltier-Pain, Gyula Dekany, Christophe Pain, Pierre Chassagne, Nicolas Fierfort, Dóra Molnàr-Gàbor
Abstract: A crystalline LNnT polymorph IV, characterized in that it displays X-ray powder diffraction reflections, based on a measurement using CuK? radiation, at 8.16, 15.41, 39.14, 23.77, 7.77 and 31.15 2? angles, and a crystalline LNnT polymorph V, characterized in that it displays X-ray powder diffraction reflections, based on a measurement using CuK? radiation, at 9.15, 10.26, 19.68, 26.06, 20.61 and 1 1.89 2? angles, are provided.