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1. 发明申请

WO2015032413A1 FERMENTATIVE PRODUCTION OF OLIGOSACCHARIDES 审中-公开
标题翻译：低聚糖的生产
公开(公告)号：WO2015032413A1
公开(公告)日：2015-03-12
申请号：PCT/DK2014/050273
申请日：2014-09-05
申请人： GLYCOM A/S
发明人： DEKANY, Gyula , PELTIER-PAIN, Pauline , MOLNÁR-GÁBOR, Dóra , HEDEROS, Markus
IPC分类号： C12P19/26 , C12P19/18 , C07H3/06
CPC分类号： C12P19/18 , C07H3/06 , C08B37/006 , C12P19/00 , C12P19/26 , C12Y204/01065 , C12Y204/01087 , C12Y204/01099
摘要： 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.
摘要翻译：本申请公开了一种生产至少四个单糖单元的寡糖的方法，有利地是HMO，特别是仅四个单糖单元的HMO，所述方法包括以下步骤：在含有岩藻糖基化的唾液酸化或N- 乙酰基 - 葡糖胺化的乳糖三糖作为受体，一种遗传修饰的细胞，其具有编码能够修饰至少四个单糖单元的寡糖的生物合成途径中的所述受体或必需中间体的酶的重组基因，有利地是HMO，特别是来自所述受体的仅四种单糖单元的HMO。

2. 发明申请

WO2013182206A1 METHOD FOR PRODUCING OLIGOSACCHARIDES AND OLIGOSACCHARIDE GLYCOSIDES BY FERMENTATION 审中-公开
标题翻译：通过发酵生产低聚葡萄糖苷和低聚果糖苷的方法
公开(公告)号：WO2013182206A1
公开(公告)日：2013-12-12
申请号：PCT/DK2013/050182
申请日：2013-06-07
申请人： GLYCOM A/S
发明人： PELTIER-PAIN, Pauline , DEKANY, Gyula , DUREAU, Remy , RISINGER, Christian , HEDEROS, Markus , CHAMPION, Elise
IPC分类号： C12P19/44 , C07H3/06 , C07H5/04 , C07H5/08 , C07H15/18 , C12P19/28 , C12P19/64
CPC分类号： C07H3/06 , C07H5/04 , C07H15/10 , C07H15/14 , C07H15/18 , C12P19/28 , C12P19/44 , C12P19/64 , Y02P20/55
摘要： 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.
摘要翻译：本申请公开了一种用于制备异头保护的糖苷寡糖衍生物的方法，其包括在含有异头保护的乳糖受体的培养基中培养具有编码可转移糖基残基的糖基转移酶的重组基因的遗传修饰细胞的步骤活化的糖核苷酸与所述乳糖受体。本申请进一步公开了一种生产寡糖的方法，包括以下步骤：（a）在含有异头保护的乳糖受体的培养基中培养具有编码可转移糖基残基的糖基转移酶的重组基因的遗传修饰细胞的活性糖核苷酸与所述乳糖受体产生异头保护的糖苷寡糖衍生物，然后（b）去除/去保护端基异构保护基。

3. 发明申请

WO2012007588A1 SYNTHESIS OF NEW SIALOOLIGOSACCHARIDE DERIVATIVES 审中-公开
标题翻译：新型SIALOOLIGOSACCHARIDE衍生物的合成
公开(公告)号：WO2012007588A1
公开(公告)日：2012-01-19
申请号：PCT/EP2011/062184
申请日：2011-07-15
申请人： GLYCOM A/S , SCHROVEN, Andreas , CHAMPION, Elise , DEKANY, Gyula , RÖHRIG, Christoph , VRASIDAS, Ioannis , PÉREZ FIGUEROA, Ignacio , HEDEROS, Markus , BOUTET, Julien , ÁGOSTON, Ágnes , KOVÁCS-PÉNZES, Piroska , HORVÁTH, Ferenc , RISINGER, Christian , PIPA, Gergely , DEMKÓ, Sándor , KRÖGER, Lars
发明人： SCHROVEN, Andreas , CHAMPION, Elise , DEKANY, Gyula , RÖHRIG, Christoph , VRASIDAS, Ioannis , PÉREZ FIGUEROA, Ignacio , HEDEROS, Markus , BOUTET, Julien , ÁGOSTON, Ágnes , KOVÁCS-PÉNZES, Piroska , HORVÁTH, Ferenc , RISINGER, Christian , PIPA, Gergely , DEMKÓ, Sándor , KRÖGER, Lars
IPC分类号： C12P19/26
CPC分类号： C07H5/04 , C07H1/06 , C07H3/06 , C12P19/14 , C12P19/18 , C12P19/26 , C12P19/44 , Y02P20/55
摘要： 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 α-sialyl moiety and the other is H, X 1 represents a carbohydrate linker,A is a D-glucopyranosyl unit optionally substituted with fucosyl, R 1 is a protecting group that is removable by hydrogenolysis, the integer m is 0 or 1, by a transsialidation reaction.
摘要翻译：本发明涉及一种合成通式（1A）化合物及其盐的方法，其中一个R基团为α-唾液酰基部分，另一个为H，X1为碳水化合物接头，A为D-吡喃葡萄糖基任选被岩藻糖基取代的单元，R 1是通过氢解可除去的保护基，整数m为0或1，通过反式磺化反应。

4. 发明申请

WO2014167538A1 SYNTHESIS OF SIALYLATED/FUCOSYLATED HUMAN MILK OLIGOSACCHARIDES 审中-公开
标题翻译：异亮氨酸/ FOSOSLIL人乳酪寡糖的合成
公开(公告)号：WO2014167538A1
公开(公告)日：2014-10-16
申请号：PCT/IB2014/060648
申请日：2014-04-11
申请人： GLYCOM A/S
发明人： CHASSAGNE, Pierre , KHANZHIN, Nikolay , HEDEROS, Markus , CHAMPION, Elise , MATWIEJUK, Martin , DEKANY, Gyula
IPC分类号： C07H1/00 , C07H5/04
CPC分类号： C07H5/04 , C07H1/00
摘要： This invention relates to achemo-enzymatic synthesis of oligosaccharides of formula 1 I 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 leastone 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.
摘要翻译：本发明涉及式Ⅰ的寡糖的急速 - 酶合成，其中R选自-OH，-N 3和-OR 6，其中R 6选自任选被一个或多个甲基取代的烯丙基，炔丙基任选地被一个或多个更多的甲基，2-三甲基甲硅烷基 - 乙基， - （CH 2）n -NH 2和 - （CH 2）n -N 3其中整数n为10，优选2或3，R选自唾液酰基部分，-SO 3 H和-CH（R）-COOH其中R选自H，烷基和苄基，R 2选自H和岩藻糖基，R 3选自H和唾液酸，R 4选自H和岩藻糖基，条件是在 R 3和R 4的leastone为H，且A为二价连接基的碳水化合物，其具有重要的生物活性和用于医药和食品工业显著商业价值。

5. 发明申请

WO2013091660A1 A METHOD FOR OBTAINING CRYSTALLINE LACTO-N-TETRAOSE AND LACTO-N-NEOTETRAOSE PRECURSORS AND MIXTURES THEREOF 审中-公开
标题翻译：用于获得结晶LACTO-N-TETRAOSE和LACTO-N- NEOTETRAOSE前体及其混合物的方法
公开(公告)号：WO2013091660A1
公开(公告)日：2013-06-27
申请号：PCT/DK2012/050502
申请日：2012-12-21
申请人： GLYCOM A/S
发明人： HEDEROS, Markus , DEKANY, Gyula , MATWIEJUK, Martin , DUREAU, Rémy , FIGUEROA PÉREZ, Ignacio
IPC分类号： C07H1/00 , C07H1/06 , C07H5/04 , C07H15/18
CPC分类号： C07H1/00 , C07H1/06 , C07H5/04 , C07H15/18
摘要： A mixture of, preferably a mixture consisting essentially of, an lacto-N-tetraose (LNT) precursor (1) and an lacto-N-neotetraose (LNnT) precursor (2), (formula 1, 2), where R is a group removable by hydrogenolysis and R 3 is either a group removable by hydrogenolysis or H, a method of crystallizing 1 and/or 2 from said mixture, and the use of said mixture for making a mixture consisting essentially of LNnT and LNT for use as a pharmaceutically or nutritionally active ingredient. The precursors can be made by reacting an acceptor of formula 5, (formula 5), wherein R is a group removable by hydrogenolysis, R 1 is acyl, Ri is acyl or H, R3 is selected from a group removable by hydrogenolysis, acyl, silyl and an acetal type group and Y is selected from alkanoylamido, haloalkanoylamido, -NAc2, benzamido, alkoxycarbonylamino, haloalkoxycarbonylamino, benzyloxycarbonylamino, azido, phthalimido, tetrachlorophthalimido, 2,3- diphenylmaleimido and 2,3-dimethylmaleimido, with a donor of formula 6, (formula 6), wherein R 4 is acyl and Xi is selected from halogen, -OC(=NH)CCl 3 , -OAc, -OBz or -SR 5 , wherein R 5 is selected from alkyl, substituted phenyl and unsubstituted phenyl, followed by one or more deprotection steps.
摘要翻译：基本上由乳-N-四糖（LNT）前体（1）和乳-N-新四糖（LNnT）前体（2）（式1，2）组成的混合物，其中R为通过氢解可除去的基团，R 3是通过氢解或H可除去的基团，从所述混合物中结晶1和/或2的方法，以及使用所述混合物制备基本上由LNnT和LNT组成的混合物用作药物或营养活性成分。前体可以通过使式5的受体（式5）反应制备，其中R是通过氢解除去的基团，R 1是酰基，R 1是酰基或H，R 3选自可以通过氢解除去的基团，酰基，甲硅烷基和缩醛型基团，Y选自式6的供体的烷酰氨基，卤代烷酰氨基，-NAc2，苯甲酰氨基，烷氧基羰基氨基，卤代烷氧基羰基氨基，苄氧基羰基氨基，叠氮基，苯二酰亚胺基，四氯邻苯二甲酰亚氨基，2,3-二苯基马来酰亚氨基和2,3-二甲基马来酰亚胺基，（式6），其中R 4是酰基，X 1选自卤素，-OC（= NH）CCl 3，-OAc，-OBz或-SR 5，其中R 5选自烷基，取代的苯基和未被取代的苯基，更多的脱保护步骤。

6. 发明申请

WO2012156898A1 DIVERSIFICATION OF HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF 审中-公开
标题翻译：人乳清蛋白（HMOs）或其前体的多样性
公开(公告)号：WO2012156898A1
公开(公告)日：2012-11-22
申请号：PCT/IB2012/052401
申请日：2012-05-14
申请人： GLYCOM A/S , DEKANY, Gyula , CHAMPION, Elise , SCHROVEN, Andreas , HEDEROS, Markus
发明人： DEKANY, Gyula , CHAMPION, Elise , SCHROVEN, Andreas , HEDEROS, Markus
IPC分类号： C07H5/04 , C07H1/00 , C07H3/06
CPC分类号： C12P19/14 , C07H1/00 , C07H5/04 , C07H13/04 , C12P19/04 , C12P19/12
摘要： 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 the steps of 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: (2) wherein R is a group removable by hydrogenolysis, R 1 independently of each other is fucosyl or H, R 4 independently of each other is sialyl or H, provided that the compound of general formula 2 is not R-glycoside of lactose, if provided alone; optionally sialylated and/or fucosylated lactose derivatives of general formula 4 and salts thereof: (4) wherein R 1 independently of each other is fucosyl or H, R 4 independently of each other is sialyl or H, provided that the compound of general formula 4 is not lactose, if provided alone; lacto-N-tetraose (LNT): (I) lacto-N-tetraose (LNT) derivatives of the following formula: (II) wherein R is a group removable by hydrogenolysis; lacto-N-neotetraose (LNnT): (III) lacto-N-neotetraose (LNnT) derivatives of the following formula: (IV) wherein R is a group removable by hydrogenolysis; 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).
摘要翻译：人乳寡糖（HMO）或其前体多样化的方法，可通过该方法获得的化合物以及涉及这些化合物的用途和组合物。该方法包括以下步骤：a）提供至少一种化合物或选自以下的化合物或混合物：选自唾液酸化的和/或通式2的岩藻糖基化的乳糖衍生物及其盐：（2）其中R是基团通过氢解除去，R 1彼此独立地是岩藻糖基或H，R 4彼此独立地是唾液酸或H，条件是通式2的化合物不是单独提供的乳糖的R-糖苷; 任选的通式4的唾液酸化和/或岩藻糖化的乳糖衍生物及其盐：（4）其中R 1彼此独立地是岩藻糖基或H，R 4彼此独立地是唾液酸或H，条件是通式4的化合物不是乳糖，如果单独提供; 乳糖-N-四糖（LNT）：（I）乳-N-差氮（LNT）衍生物：（II）其中R是可通过氢解除去的基团; 乳酸-N-新四糖（LNnT）：（III）下式的乳-N-新四糖（LNnT）衍生物：（Ⅳ）其中R是通过氢解除去的基团; b）向所述至少一种化合物或根据步骤a）提供的化合物的混合物中加入至少一种包含转糖苷酶活性的酶; 和c）孵育根据步骤b）获得的混合物。

7. 发明申请

WO2012155916A1 MANUFACTURE OF LACTO-N-TETRAOSE 审中-公开
标题翻译： LACTO-N-TETRA的制备
公开(公告)号：WO2012155916A1
公开(公告)日：2012-11-22
申请号：PCT/DK2012/050170
申请日：2012-05-14
申请人： GLYCOM A/S , HEDEROS, Markus , DEKANY, Gyula , DEMKÓ, Sándor , KOVÁCS, Imre , BAJZA, István
发明人： HEDEROS, Markus , DEKANY, Gyula , DEMKÓ, Sándor , KOVÁCS, Imre , BAJZA, István
IPC分类号： C07H1/00 , C07H15/12
CPC分类号： C07H15/20 , C07H1/00 , C07H13/04 , C07H15/18
摘要： The present invention relates to the synthesis of the tetrasaccharide of formula (I) and novel intermediates used in the synthesis.
摘要翻译：本发明涉及式（I）的四糖和合成中使用的新中间体的合成。

8. 发明授权

EP2536736B1 PRODUCTION OF 6'-O-SIALYLLACTOSE AND INTERMEDIATES 有权
标题翻译：生产6'-O-唾液酸糖和中间体
公开(公告)号：EP2536736B1
公开(公告)日：2017-08-16
申请号：EP11744297.0
申请日：2011-02-21
申请人： Glycom A/S
发明人： PÉREZ FIGUEROA, Ignacio , HORVÁTH, Ferenc , DEKANY, Gyula , ÁGOSTON, Károly , ÁGOSTON, Ágnes , BAJZA, István , BOUTET, Julien , HEDEROS, Markus , KOVÁCS-PÉNZES, Piroska , KRÖGER, Lars , RÖHRIG, Christoph , SCHROVEN, Andreas , VRASIDAS, Ioannis , RISINGER, Christian
IPC分类号： C07H1/00 , C07H13/04 , C07H15/18
CPC分类号： A23L1/308 , A23L33/10 , A23L33/21 , A61K31/702 , C07H1/00 , C07H3/06 , C07H13/04 , C07H15/18

9. 发明授权

EP2417143B1 SYNTHESIS OF 2'-O-FUCOSYLLACTOSE 有权
标题翻译： 2'-O-岩藻糖的合成
公开(公告)号：EP2417143B1
公开(公告)日：2016-12-21
申请号：EP10715191.2
申请日：2010-04-07
申请人： Glycom A/S
发明人： DÉKANY, Gyula , ÁGOSTON, Károly , BAJZA, Istvan , BOUTET, Julien , BØJSTRUP, Marie , FANEFJORD, Mette , FIGUEROA PÉREZ, Ignacio , HEDEROS, Markus , HORVÁTH, Ferenc , KOVÁCS-PÉNZES, Piroska , KRÖGER, Lars , OLSSON, Johan , RÖHRIG, Christoph , SCHROVEN, Andreas , VRASIDAS, Ioannis
IPC分类号： C07H3/06 , C07H15/04 , C07H15/203 , C07H1/00
CPC分类号： C07H3/06 , C07H1/00 , C07H15/04 , C07H15/203

10. 发明公开

EP2707493A1 METHOD FOR GENERATING HUMAN MILK OLIGOSACCHARIDES (HMOs) OR PRECURSORS THEREOF 审中-公开
标题翻译：用于生产人乳寡糖或其前体
公开(公告)号：EP2707493A1
公开(公告)日：2014-03-19
申请号：EP12785846.2
申请日：2012-05-14
申请人： Glycom A/S
发明人： DEKANY, Gyula , CHAMPION, Elise , SCHROVEN, Andreas , HEDEROS, Markus
IPC分类号： C12P19/18 , C07H5/04 , C07H17/02 , C07H17/04 , C12P19/44
CPC分类号： C12P19/14 , A23L33/40 , C07H9/06 , C07H17/02 , C07H17/04 , C07H17/075 , C07H19/01 , C08B37/006 , C12P19/04 , C12P19/12 , C12P19/18 , C12Y302/0114
摘要： 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).

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