Patents Assigned to Glycom A/S
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Publication number: 20150329579Abstract: A method for making an N-substituted D-mannosamine derivative of the following formula 1 and its salts wherein R1 is a non-electron-withdrawing group, and wherein R2 is —OH or R2 is —NHR3 wherein R3 is a group removable by hydrogenolysis; by epimerizing an N-substituted D-glucosamine derivative of the following formula 2 wherein R1 and R2 are as defined above.Type: ApplicationFiled: December 20, 2013Publication date: November 19, 2015Applicant: GLYCOM A/SInventors: Ioannis VRASIDAS, Gábor VLÁD, Gyula DEKANY
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Patent number: 9187513Abstract: A compound of the formula (1) wherein R1 is a group removable by hydrogenolysis, and wherein R2 is OH or R2 is —NHR3 wherein R3 is a group removable by hydrogenolysis. The compound can be made from fructose by a Heyns-rearrangement. The compound can be used then to make free D-mannosamine or its salts, D-mannosamine building blocks and mannosamine containing oligo- or polysaccharides, N-acetyl-D-mannosamine and its hydrates and solvates, neuraminic acid derivatives, and viral neuraminidase inhibitors.Type: GrantFiled: April 11, 2012Date of Patent: November 17, 2015Assignee: GLYCOM A/SInventors: Ioannis Vrasidas, Gyula Dekany, Ågnes Jánosi, Markus Hederos, Christoph Röhrig
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Patent number: 9102966Abstract: The invention relates to a method for the synthesis of compounds of general formula (1A) and salts thereof wherein one of the R groups is an ?-sialyl moiety and the other is H, X1 represents a carbohydrate linker, A is a D-glucopyranosyl unit optionally substituted with fucosyl, R1 is a protecting group that is removable by hydrogenolysis, the integer m is 0 or 1, by a transsialidation reaction.Type: GrantFiled: July 15, 2011Date of Patent: August 11, 2015Assignee: GLYCOM A/SInventors: Andreas Schroven, Elise Champion, Gyula Dekany, Christoph Röhrig, Ioannis Vrasidas, Ignacio Figueroa Pérez, Markus Hederos, Julien Boutet, Ágnes Ágoston, Piroska Kovács-Pénzes, Ferenc Horváth, Christian Risinger, Gergely Pipa, Sándor Demkó, Lars Kröger
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Publication number: 20150183814Abstract: 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: ApplicationFiled: June 14, 2013Publication date: July 2, 2015Applicant: Glycom A/SInventors: Andreas Schroven, Gyula Dekany, Peter Erdmann, Andrea Schwarz
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Publication number: 20150182549Abstract: A method for modifying galactosyl disaccharides in order to enhance their bifidogenic effect, comprising reacting at least one glycosyl donor with a precursor galactosyl disaccharide or a mixture of precursor galactosyl disaccharides using enzyme catalysis, compounds obtainable by said method and the use of such compounds in consumable products.Type: ApplicationFiled: June 24, 2013Publication date: July 2, 2015Applicant: Glycom A/SInventors: Elise Champion, Dóra Molnár-Gábor, Gyula Dekany
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Publication number: 20150183816Abstract: The invention relates to a method for making modified galactooligosaccharides comprising the step of enzymatic glycosylation, the modified galactooligosaccharides obtainable by the method and consumable products containing them.Type: ApplicationFiled: June 24, 2013Publication date: July 2, 2015Applicant: Glycom A/SInventors: Elise Champion, Dóra Molnár-Gábor, Gyula Dekany
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Publication number: 20150133647Abstract: The application discloses a method for producing anomerically protected glycosidic oligosaccharide derivatives comprising the step of culturing, in a culture medium containing an anomerically protected lactose acceptor, a genetically modified cell having a recombinant gene that encodes a glycosyl transferase that can transfer a glycosyl residue of an activated sugar nucleotide to said lactose acceptor. The application further discloses a method for producing an oligosaccharide comprising the steps of: (a) culturing, in a culture medium containing an anomerically protected lactose acceptor, a genetically modified cell having a recombinant gene that encodes a glycosyl transferase that can transfer a glycosyl residue of an activated sugar nucleotide to said lactose acceptor to produce an anomerically protected glycosidic oligosaccharide derivative, then (b) removing/deprotecting the anomeric protective group.Type: ApplicationFiled: June 7, 2013Publication date: May 14, 2015Applicant: Glycom A/SInventors: Pauline Peltier-Pain, Gyula Dekany, Rémy Dureau, Christian Risinger, Markus Hederos, Elise Champion
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Patent number: 9012625Abstract: The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.Type: GrantFiled: April 7, 2010Date of Patent: April 21, 2015Assignee: Glycom A/SInventors: Gyula Dékany, Károly Ágoston, Istvan Bajza, Julien Boutet, Marie Bøjstrup, Mette Fanefjord, Ignacio Pérez Figueroa, Markus Hederos, Ferenc Horvath, Piroska Kovács-Pénzes, Lars Kröger, Johan Olsson, Christoph Röhrig, Andreas Schroven, Ioannis Vrasidas
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Patent number: 8993740Abstract: The present invention relates to a method for preparation of the tetrasaccharide lacto-N-neotetraose (LNnt, formula (I)) especially in large scale, as well as intermediates in the synthesis, a new crystal form (polymorph) of LNnt, and the use thereof in pharmaceutical or nutritional compositions.Type: GrantFiled: February 21, 2011Date of Patent: March 31, 2015Assignee: Glycom A/SInventors: István Bajza, Gyula Dekany, Károly Ágoston, Ignacio Figuero-Pérez, Julien Boutet, Markus Hederos, Ferenc Horváth, Piroska Kovács-Pénzes, Lars Kröger, Christoph Röhrig, Andreas Schroven, Ioannis Vrasidas, Péter Trinka, László Kalmár, Irme Kovács, Sándor Demkó, Ágnes Ágoston, Christian Risinger
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Patent number: 8927698Abstract: The present invention relates to an improved synthesis of a trisaccharide of the formula, novel intermediates used in the synthesis and the preparation of the intermediates.Type: GrantFiled: April 7, 2010Date of Patent: January 6, 2015Assignee: Glycom A/SInventors: Gyula Dékany, Istvan Bajza, Julien Boutet, Ignacio Pérez Figueroa, Markus Hederos, Ferenc Horvath, Piroska Kovács-Pénzes, Lars Kröger, Johan Olsson, Christoph Röhrig, Andreas Schroven, Ioannis Vrasidas
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Publication number: 20140378679Abstract: ?-Lactosamine hydrochloride, substantially free of ?-lactosamine hydrochloride; a method of preparing ?-lactosamine hydrochloride monohydrate from an anomeric mixture of lactosamine hydrochloride, including: preparing a solution including the anomeric mixture of lactosamine hydrochloride, water and at least one water-miscible organic solvent at a temperature of 0-100° C., and cooling the solution to cause crystallisation of ?-lactosamine hydrochloride monohydrate; a method of preparing anhydrous ?-lactosamine hydrochloride; and use of ?-lactosamine hydrochloride as a food supplement or intermediate in synthesis.Type: ApplicationFiled: July 1, 2014Publication date: December 25, 2014Applicant: GLYCOM A/SInventors: Gyula DEKANY, Károly ÁGOSTON, István BAJZA, Marie BØJSTRUP, Ignacio FIGUEROA PÉREZ, Lars KRÖGER, Christoph H. RÖHRIG
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Patent number: 8901291Abstract: The present application discloses a method for the crystallization of fucose, characterized in that the crystallization is carried out from a mixture comprising fucose and at least one 6-deoxy sugar selected from 6-deoxy-talose and 6-deoxy-gulose. In one embodiment, the mixture comprises fucose and 6-deoxy-talose.Type: GrantFiled: May 19, 2011Date of Patent: December 2, 2014Assignee: Glycom A/SInventors: Julien Boutet, Gyula Dekany, Ágnes Jànosi, Gergely Pipa, Ferenc Horvàth, Krisztián Kovàcs, Ignacio Pérez Figueroa, Markus Hederos, Andreas Schroven, Ioannis Vrasidas, Piroska Kovács-Pénzes, Christian Risinger, Sándor Demkò, Lars Kröger, Christoph Röhrig
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Publication number: 20140349347Abstract: Method of making NANA from NAM, which may itself be made from fructose. The NAM is treated with pyruvic acid or a pyruvate in the presence of a NANA aldolase having at least 70% sequence similarity or homology to the amino acid sequence of SEQ. ID. NO. 1.Type: ApplicationFiled: October 10, 2012Publication date: November 27, 2014Applicant: Glycom A/SInventors: Andreas Schroven, Gyula Dekany, Ionnis Vrasidas
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Patent number: 8889637Abstract: The present invention relates to novel polymorphs of the trisaccharide 2?-O-fucosyllactose (2-FL) of formula (1), methods for producing said polymorphs and their use in pharmaceutical or nutritional compositions.Type: GrantFiled: June 1, 2011Date of Patent: November 18, 2014Assignee: Glycom A/SInventors: Károly Ágoston, István Bajza, Gyula Dekany, Péter Trinka, Ágnes Ágoston, Gábor Kádár, Sándor Demkó, Ignacio Figueroa-Pérez, Markus Hederos, Ferenc Horváth, Andreas Schroven, Ioannis Vrasidas, Piroska Kovács-Pénzes, Christian Risinger, László Kalmár, Gergely Pipa, Julien Boutet, Lars Kröger, Christoph Röhrig
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Publication number: 20140234912Abstract: A method for generating human milk oligosaccharides (HMOs) or precursors thereof, compounds obtainable by the method, and uses and compositions involving such compounds. The method comprising the steps of a) providing at least one donor selected from the group of compounds of any of formulae 5 to 10, b) providing at least one acceptor from a group of lactose, LNT, LNnT and derivatives thereof, c) providing at least one enzyme comprising a transglycosidase activity and/or a glycosynthase activity, d) preparing a mixture of the at least one donor, at least one acceptor and at least one enzyme provided in steps a), b) and c); and e) incubating the mixture prepared according to step d).Type: ApplicationFiled: May 14, 2012Publication date: August 21, 2014Applicant: GLYCOM A/SInventors: Gyula Dekany, Elise Champion, Andreas Schroven, Markus Hederos
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Publication number: 20140235848Abstract: A method that can be used to make a precursor of L-fucose from D-glucose that includes the steps of a) making a compound of formula (1) from D-glucose, formula (1) wherein R1 is acyloxy, and Q is a group (a), (b), (c) or (d), formula (a), (b), (c) or (d) or wherein R1 is OH, and Q is a group (e), (f) or (g); formula (e), (f) or (g) wherein R2 is acyloxy and R3 is a sulphonyl leaving group; and b) producing 6-deoxy-L-talose from the compound of formula (1) formed in step a), wherein the moiety is a highly lipophilic protecting group; compounds according to formula (1), and use of a compound according to formula (1) are provided.Type: ApplicationFiled: September 28, 2012Publication date: August 21, 2014Applicant: Glycom A/SInventors: Julien BOUTET, Nikolay KHANZHIN, Filippo BONACCORSI, Gyula DEKANY
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Publication number: 20140228554Abstract: A method for the synthesis of a fucooligosaccharide glycosides by reacting a fucosyl donor with H-A-R1 or a salt thereof, wherein A and R1 are as defined herein, under the catalysis of an enzyme capable of transferring fucose is provided. The fucooligosaccharid glycoside compounds, or derivatives thereof, their use in the manufacture of human milk oligosaccharides, and a method of manufacture of human milk oligosaccharides, are also provided.Type: ApplicationFiled: March 19, 2012Publication date: August 14, 2014Applicant: Glycom A/SInventors: Elise Champion, Gyula Dekany, Markus Hederos, Karoly Agoston
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Patent number: 8802841Abstract: A 1,2-dideoxy-1,2-diamino oligosaccharide or polysaccharide in its free base, salt or metal-complex form as shown in General Formula 1 and derivative thereof is described. R1, R2 and R3 are each independently selected from the group consisting of H and a carbohydrate moiety, with the proviso that at least one of the groups R1, R2 or R3 is a carbohydrate moiety; R4 is selected from the group consisting of: H, optionally substituted C1-20-alkyl, optionally substituted heteroalkyl, optionally substituted C2-20-alkenyl, optionally substituted C2-20-alkynyl, optionally substituted C3-10-cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl.Type: GrantFiled: November 3, 2008Date of Patent: August 12, 2014Assignee: Glycom A/SInventors: Gyula Dekany, István Bajza, Marie Bøjstrup, Károly Ágoston, Lars Kröger, Ignacio Figueroa Pérez, Christoph H. Röhrig, Paulo Vital, Erzsébet Czinege
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Patent number: 8796434Abstract: ?-Lactosamine hydrochloride, substantially free of ?-lactosamine hydrochloride; a method of preparing ?-lactosamine hydrochloride monohydrate from an anomeric mixture of lactosamine hydrochloride, including: preparing a solution including the anomeric mixture of lactosamine hydrochloride, water and at least one water-miscible organic solvent at a temperature of 0-100° C., and cooling the solution to cause crystallization of ?-lactosamine hydrochloride monohydrate; a method of preparing anhydrous ?-lactosamine hydrochloride; and use of ?-lactosamine hydrochloride as a food supplement or intermediate in synthesis.Type: GrantFiled: July 15, 2009Date of Patent: August 5, 2014Assignee: Glycom A/SInventors: Gyula Dekany, Károly Ágoston, István Bajza, Marie Bøjstrup, Ignacio Fegueroa Pérez, Lars Kröger, Christoph H. Röhrig
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Publication number: 20140212930Abstract: 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: ApplicationFiled: May 14, 2012Publication date: July 31, 2014Applicant: GLYCOM A/SInventors: Gyula Dekany, Elise Champion, Andreas Schroven, Markus Hederos