Patents Assigned to Glycom A/S
  • Publication number: 20170175154
    Abstract: The invention relates to a genetically modified microorganism for making a recombinant oligosaccharide, preferably of 3-8 monosaccharide units, more preferably of 3-5 monosaccharide units, particularly a HMO, which comprises one or more genes encoding a sucrose utilization system, so the microorganism can use sucrose as a carbon and energy source. The one or more genes encoding a sucrose utilization system are preferably one or more genes encoding a heterologous PTS-dependent sucrose utilization transport system, such as the scr genes.
    Type: Application
    Filed: June 29, 2015
    Publication date: June 22, 2017
    Applicant: GLYCOM A/S
    Inventors: Eric Samain, Pauline Peltier-Pain, Katrine Bych, Ted Johanson, Elise Champion, Gyula Dekany
  • Publication number: 20160289721
    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: Application
    Filed: May 23, 2016
    Publication date: October 6, 2016
    Applicant: GLYCOM A/S
    Inventors: Gyula DEKANY, Elise Champion, Markus Hederos
  • Publication number: 20160215315
    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: Application
    Filed: September 5, 2014
    Publication date: July 28, 2016
    Applicant: Glycom A/S
    Inventors: Gyula Dekany, Pauline Peltier-Pain, Dóra Molnár-Gábor, Markus Hederos
  • Patent number: 9382564
    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 14, 2012
    Date of Patent: July 5, 2016
    Assignee: GLYCOM A/S
    Inventors: Gyula Dekany, Elise Champion, Andreas Schroven, Markus Hederos
  • Publication number: 20160075729
    Abstract: An achemo-enzymatic synthesis of oligosaccharides of formula 1 is presented wherein R is selected from —OH, —N3 and —OR6 wherein R6 is selected from allyl optionally substituted by one or more methyl, propargyl optionally substituted by one or more methyl, 2-trimethylsilyl-ethyl, —(CH2)n—NH2 and —(CH2)n—N3 wherein integer n is to 10, preferably 2 or 3, R is selected from sialyl moiety, —SO3H and —CH(R)—COOH wherein R is selected from H, alkyl and benzyl, R2 is selected from H and fucosyl, R3 is selected from H and sialyl, R4 is selected from H and fucosyl, provided that at least one of R3 and R4 is H, and A is a divalent carbohydrate linker, having important biological activities and significant commercial value for the pharmaceutical and food industry.
    Type: Application
    Filed: April 11, 2014
    Publication date: March 17, 2016
    Applicant: GLYCOM A/S
    Inventors: Pierre CHASSAGNE, Nikolay KHANZHIN, Markus HEDEROS, Elise CHAMPION, Martin MATWIEJUK, Gyula DEKANY
  • Publication number: 20160024129
    Abstract: 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 in is 0 or 1, by a transsialidation reaction.
    Type: Application
    Filed: July 6, 2015
    Publication date: January 28, 2016
    Applicant: GLYCOM A/S
    Inventors: Andreas SCHROVEN, Elise Champion, Gyula Dekany
  • Patent number: 9237764
    Abstract: The present invention relates to a method for preparation of the trisaccharide 6?-O-sialyllactose (formula (I)) or salts thereof as well as intermediates in the synthesis and for the use of 6?-O-sialyllactose salts in pharmaceutical or nutritional compositions.
    Type: Grant
    Filed: February 21, 2011
    Date of Patent: January 19, 2016
    Assignee: Glycom A/S
    Inventors: Ignacio Figueroa Pérez, Ferenc Horváth, Gyula Dekany, Károly Ágoston, Ágnes Ágoston, István Bajza, Julien Boutet, Markus Hederos, Piroska Kovács-Pénzes, Lars Kröger, Christoph Röhrig, Andreas Schroven, Ioannis Vrasidas, Christian Risinger
  • Patent number: 9234225
    Abstract: 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: Grant
    Filed: May 14, 2012
    Date of Patent: January 12, 2016
    Assignee: GLYCOM A/S
    Inventors: Gyula Dekany, Elise Champion, Andreas Schroven, Markus Hederos
  • Publication number: 20150329579
    Abstract: 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: Application
    Filed: December 20, 2013
    Publication date: November 19, 2015
    Applicant: GLYCOM A/S
    Inventors: Ioannis VRASIDAS, Gábor VLÁD, Gyula DEKANY
  • Patent number: 9187513
    Abstract: 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: Grant
    Filed: April 11, 2012
    Date of Patent: November 17, 2015
    Assignee: GLYCOM A/S
    Inventors: Ioannis Vrasidas, Gyula Dekany, Ågnes Jánosi, Markus Hederos, Christoph Röhrig
  • Patent number: 9102966
    Abstract: 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: Grant
    Filed: July 15, 2011
    Date of Patent: August 11, 2015
    Assignee: GLYCOM A/S
    Inventors: 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
  • Publication number: 20150183816
    Abstract: 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: Application
    Filed: June 24, 2013
    Publication date: July 2, 2015
    Applicant: Glycom A/S
    Inventors: Elise Champion, Dóra Molnár-Gábor, Gyula Dekany
  • Publication number: 20150182549
    Abstract: 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: Application
    Filed: June 24, 2013
    Publication date: July 2, 2015
    Applicant: Glycom A/S
    Inventors: Elise Champion, Dóra Molnár-Gábor, Gyula Dekany
  • Publication number: 20150183814
    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: Application
    Filed: June 14, 2013
    Publication date: July 2, 2015
    Applicant: Glycom A/S
    Inventors: Andreas Schroven, Gyula Dekany, Peter Erdmann, Andrea Schwarz
  • Publication number: 20150133647
    Abstract: 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: Application
    Filed: June 7, 2013
    Publication date: May 14, 2015
    Applicant: Glycom A/S
    Inventors: Pauline Peltier-Pain, Gyula Dekany, Rémy Dureau, Christian Risinger, Markus Hederos, Elise Champion
  • Patent number: 9012625
    Abstract: 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: Grant
    Filed: April 7, 2010
    Date of Patent: April 21, 2015
    Assignee: Glycom A/S
    Inventors: 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
  • Patent number: 8993740
    Abstract: 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: Grant
    Filed: February 21, 2011
    Date of Patent: March 31, 2015
    Assignee: Glycom A/S
    Inventors: 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
  • Patent number: 8927698
    Abstract: 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: Grant
    Filed: April 7, 2010
    Date of Patent: January 6, 2015
    Assignee: Glycom A/S
    Inventors: 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
  • Publication number: 20140378679
    Abstract: ?-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: Application
    Filed: July 1, 2014
    Publication date: December 25, 2014
    Applicant: GLYCOM A/S
    Inventors: Gyula DEKANY, Károly ÁGOSTON, István BAJZA, Marie BØJSTRUP, Ignacio FIGUEROA PÉREZ, Lars KRÖGER, Christoph H. RÖHRIG
  • Patent number: 8901291
    Abstract: 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: Grant
    Filed: May 19, 2011
    Date of Patent: December 2, 2014
    Assignee: Glycom A/S
    Inventors: 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