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    • 2. 发明公开
      EP2686330A1 SYNTHESIS OF NEW FUCOSE-CONTAINING CARBOHYDRATE DERIVATIVES 审中-公开
    • SYNTHESIS OF NEW FUCOSE-CONTAINING CARBOHYDRATE DERIVATIVES
    • 综合新FUCOSEHALTIGER糖衍生物的
    • EP2686330A1
    • 2014-01-22
    • EP12760395.9
    • 2012-03-19
    • Glycom A/S
    • CHAMPION, Elise , DEKANY, Gyula , HEDEROS, Markus , ÁGOSTON, Károly
    • C07H5/04 , C07H5/08 , C07H7/04 , C07H17/04 , C07H1/00
    • C12P19/60 , C07H15/08 , C07H15/18 , C07H15/203 , C07H17/04 , Y02P20/55
    • A method for the synthesis of a compound of formula (1) or a salt thereof, wherein A is a carbohydrate linker which is a lactosyl moiety or which consists of a lactosyl moiety and at least one monosaccharide unit selected from the group consisting of: glucose, galactose, N-acetylglucosamine, fucose and N-acetyl neuraminic acid; and wherein R1 is one of the following anomeric protecting groups: a) -OR2, wherein R2 is a protecting group removable by catalytic hydrogenolysis; b) -SR3, wherein R3 is an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted benzyl; c) -NH- C(R")=C(R')2, wherein each R' independently is one of the following electron withdrawing groups: -CN, -COOH, -COO-alkyl, -CO-alkyl, -CONH2, -CONH- alkyl or -CON(alkyl)2, or wherein the two R'-groups are linked together and form -CO-(CH2)2-4-CO- and thus form, together with the carbon atom to which they are attached, a 5-7 membered cycloalkan-1,3-dione, in which dione any of the methylene groups is optionally substituted with 1 or 2 alkyl groups, and R" is H or alkyl, in which a fucosyl donor of formula (2) wherein X is selected from the group consisting of: a guanosine diphosphatyl moiety, a lactose moiety, azide, fluoride, optionally substituted phenoxy-, optionally substituted pyridinyloxy-, optionally substituted 3-oxo-furanyloxy- of formula (A), optionally substituted 1,3,5-triazinyloxy- of formula (B), 4-methylumbelliferyloxy-group of formula (C), and a group of formula (D) wherein Ra is independently H or alkyl, or two vicinal Ra groups represent a =C(Rb)2 group, wherein Rb is independently H or alkyl, Rc is independently selected from the group consisting of alkoxy, amino, alkylamino and dialkylamino, Rd is selected from the group consisting of H, alkyl and -C(=O)Re, wherein Re is OH, alkoxy, amino, alkylamino, dialkylamino, hydrazino, alkylhydrazino, dialkylhydrazino or trialkylhydrazino, is reacted with an acceptor of formula H-A-R1 or a salt thereof, wherein A and R1 are as defined above, under the catalysis of an enzyme capable of transferring fucose. A compound of formula 1', its use in manufacture of human milk oligosaccharides, a method of manufacture of human milk oligosaccharides, and a fucosyl donor are also provided.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Global Dossier Espacenet 法律信息 同族专利 专利引用
    • 8. 发明申请
      WO2012127410A1 SYNTHESIS OF NEW FUCOSE-CONTAINING CARBOHYDRATE DERIVATIVES 审中-公开
    • SYNTHESIS OF NEW FUCOSE-CONTAINING CARBOHYDRATE DERIVATIVES
    • 新型含羧酸的碳氢化合物衍生物的合成
    • WO2012127410A1
    • 2012-09-27
    • PCT/IB2012/051314
    • 2012-03-19
    • GLYCOM A/S , CHAMPION, Elise , DEKANY, Gyula , HEDEROS, Markus , ÁGOSTON, Károly
    • CHAMPION, Elise , DEKANY, Gyula , HEDEROS, Markus , ÁGOSTON, Károly
    • C07H5/04 , C07H5/08 , C07H7/04 , C07H17/04 , C07H1/00
    • C12P19/60 , C07H15/08 , C07H15/18 , C07H15/203 , C07H17/04 , Y02P20/55
    • A method for the synthesis of a compound of formula (1) or a salt thereof, wherein A is a carbohydrate linker which is a lactosyl moiety or which consists of a lactosyl moiety and at least one monosaccharide unit selected from the group consisting of: glucose, galactose, N -acetylglucosamine, fucose and N -acetyl neuraminic acid; and wherein R 1 is one of the following anomeric protecting groups: a) -OR 2 , wherein R 2 is a protecting group removable by catalytic hydrogenolysis; b) -SR 3 , wherein R 3 is an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted benzyl; c) -NH- C(R")=C(R') 2 , wherein each R' independently is one of the following electron withdrawing groups: -CN, -COOH, -COO-alkyl, -CO-alkyl, -CONH 2 , -CONH- alkyl or -CON(alkyl) 2 , or wherein the two R'-groups are linked together and form -CO-(CH 2 ) 2-4 -CO- and thus form, together with the carbon atom to which they are attached, a 5-7 membered cycloalkan-1,3-dione, in which dione any of the methylene groups is optionally substituted with 1 or 2 alkyl groups, and R" is H or alkyl, in which a fucosyl donor of formula (2) wherein X is selected from the group consisting of: a guanosine diphosphatyl moiety, a lactose moiety, azide, fluoride, optionally substituted phenoxy-, optionally substituted pyridinyloxy-, optionally substituted 3-oxo-furanyloxy- of formula (A), optionally substituted 1,3,5-triazinyloxy- of formula (B), 4-methylumbelliferyloxy-group of formula (C), and a group of formula (D) wherein R a is independently H or alkyl, or two vicinal R a groups represent a =C(R b ) 2 group, wherein R b is independently H or alkyl, R c is independently selected from the group consisting of alkoxy, amino, alkylamino and dialkylamino, R d is selected from the group consisting of H, alkyl and -C(=O)R e , wherein R e is OH, alkoxy, amino, alkylamino, dialkylamino, hydrazino, alkylhydrazino, dialkylhydrazino or trialkylhydrazino, is reacted with an acceptor of formula H-A-R 1 or a salt thereof, wherein A and R 1 are as defined above, under the catalysis of an enzyme capable of transferring fucose. A compound of formula 1', its use in manufacture of human milk oligosaccharides, a method of manufacture of human milk oligosaccharides, and a fucosyl donor are also provided.
    • 一种用于合成式（1）化合物或其盐的方法，其中A是作为乳糖基部分的碳水化合物接头或由乳糖基部分和至少一种选自以下的单糖单元组成的组：葡萄糖 ，半乳糖，N-乙酰氨基葡萄糖，岩藻糖和N-乙酰神经氨酸; 并且其中R 1是以下端基异构保护基之一：a）-OR 2，其中R 2是通过催化氢解除去的保护基; b）-SR 3，其中R 3是任选取代的烷基，任选取代的芳基或任选取代的苄基; c）-NH- C（R“）= C（R'）2，其中每个R'独立地是以下吸电子基团之一：-CN，-COOH，-COO-烷基，-CO-烷基，-CONH 2 ，-CONH-烷基或-CON（烷基）2，或其中两个R'基团连接在一起并形成-CO-（CH 2）2-4 -CO-，因此与它们所形成的碳原子一起形成 连接有5-7元环烷烃-1,3-二酮，其中任一亚甲基中的二酮任选被1或2个烷基取代，R“是H或烷基，其中式（ 2）其中X选自：鸟苷二磷酸基部分，乳糖部分，叠氮化物，氟化物，任选取代的苯氧基 - ，任选取代的吡啶氧基 - ，任选取代的式（A）的3-氧代 - 呋喃氧基 - ，任选地 式（B）的取代的1,3,5-三嗪基氧基，式（C）的4-甲基伞形氧代基和式（D）的基团，其中R a独立地为H或烷基，或两个邻位的R a基团表示= C（Rb）2基团，其中 R b独立地是H或烷基，R c独立地选自烷氧基，氨基，烷基氨基和二烷基氨基，Rd选自H，烷基和-C（= O）Re，其中Re是OH，烷氧基 ，氨基，烷基氨基，二烷基氨基，肼基，烷基肼基，二烷基肼基或三烷基肼，与式HA-R1的受体或其盐，其中A和R 1如上定义，在能够转移岩藻糖的酶的催化下。 还提供了式1'化合物，其在制造人乳低聚糖中的用途，制造人乳低聚糖和岩藻糖供体的方法。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Global Dossier Espacenet 法律信息 同族专利 专利引用
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