α-2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-galactose 1-phosphate | 1608127-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-galactose 1-phosphate
• CAS: 1608127-23-6
• 化学式: C₁₂H₁₈N₃O₁₁P
• 分子量: 411.262
• InChiKey: DOUBSNLOZFJBTP-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  203.65
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  α-2-azido-2-deoxy-3,4,6-tri-O-acetyl-D-galactose 1-phosphate 在 palladium on activated charcoal 、 氢气 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  PROCESS FOR THE CYCLOADDITION OF A HALOGENATED 1,3-DIPOLE COMPOUND WITH A (HETERO)CYCLOALKYNE

  摘要：

  本发明涉及一种环加成过程，包括以下步骤：将卤代脂肪1,3-二极化合物与根据式（1）的（杂）环烷炔发生反应。优选，根据式（1）的（杂）环烷炔是（杂）环辛炔。本发明还涉及根据本发明的过程获得的环加成产物。本发明还涉及卤代脂肪1,3-二极化合物，特别是包含N-乙酰半乳糖氨基葡萄糖醛酸-UDP（GalNAc-UDP）的卤代脂肪1,3-二极化合物，以及包含（过酰化的）N-乙酰葡萄糖胺（GlcNAc）、N-乙酰半乳糖氨基（GalNAc）、N-乙酰甘露糖氨基（ManNAc）和N-乙酰神经酸（NeuNAc）的卤代1,3-二极化合物。

  公开号：

  US20170008858A1

文献信息

• [EN] PROCESS FOR THE CYCLOADDITION OF A HALOGENATED 1,3-DIPOLE COMPOUND WITH A (HETERO)CYCLOALKYNE<br/>[FR] PROCÉDÉ DE CYCLOADDITION D'UN COMPOSÉ 1,3-DIPPOLE HALOGÉNÉ AVEC UN (HÉTÉRO)CYCLOALKYNE
  申请人：SYNAFFIX BV

  公开号：WO2015112016A1

  公开（公告）日：2015-07-30

  The present invention relates to a cycloaddition process comprising the step of reacting a halogenated aliphatic 1,3-dipole compound with a (hetero)cycloalkyne according to Formula (1): Preferably, the (hetero)cycloalkyne according to Formula (1) is a (hetero)cyclooctyne. The invention also relates to the cycloaddition products obtainable by the process according to the invention. The invention further relates to halogenated aliphatic 1,3- dipole compounds, in particular tohalogenated aliphatic 1,3-dipole compounds comprising N-acetylgalactosamine-UDP (GalNAc-UDP),and to halogenated 1,3- dipole compounds comprising (peracylated) N-acetylglucosamine(GlcNAc), N- acetylgalactosamine(GalNAc), N-acetylmannosamine(ManNAc)and N- acetylneuraminic acid(NeuNAc).

  本发明涉及一种环加成过程，包括将卤代脂肪1,3-二极化合物与按照式（1）反应的（杂）环烯烃化合物进行反应的步骤。优选，按照式（1）的（杂）环烯烃化合物是（杂）环辛烯。该发明还涉及根据本发明的方法获得的环加成产物。此外，该发明还涉及卤代脂肪1,3-二极化合物，特别是包括N-乙酰半乳糖氨基葡萄糖醛酸-UDP（GalNAc-UDP）的卤代脂肪1,3-二极化合物，以及包括（过酰化的）N-乙酰葡萄糖胺（GlcNAc）、N-乙酰半乳糖氨基葡萄糖醛酸（GalNAc）、N-乙酰甘露糖氨基葡萄糖醛酸（ManNAc）和N-乙酰神经酸（NeuNAc）的卤代1,3-二极化合物。
• [EN] SULFAMIDE LINKER, CONJUGATES THEREOF, AND METHODS OF PREPARATION<br/>[FR] LIEUR DE TYPE SULFAMIDE, CONJUGUÉS DE CELUI-CI ET PROCÉDÉS DE PRÉPARATION
  申请人：SYNAFFIX BV

  公开号：WO2016053107A1

  公开（公告）日：2016-04-07

  The present invention relates to a compound comprising an alpha-end and an omega-end, the compound comprising on the alpha-end a reactive group Qlcapable of reacting with a functional group F1present on a biomolecule and on the omega-end a target molecule, the compound further comprising a group according to formula (1) or a salt thereof: Said compound may also be referred to as a linker-conjugate. The invention also relates to a process for the preparation of a bioconjugate, the process comprising the step of reacting a reactive group Q1of a linker-conjugate according to the invention with a functional group F1of a biomolecule. The invention further relates to a bioconjugate obtainable by the process according to the invention. In a preferred embodiment, the invention concerns a process for the preparation of a bioconjugate via a cycloaddition, such as a (4+2)-cycloaddition (e.g. a Diels-Alder reaction) or a (3+2)-cycloaddition (e.g. a 1,3-dipolar cycloaddition).

  本发明涉及一种化合物，包括一个α端和一个ω端，该化合物在α端包括一个与生物分子上存在的功能基团F1反应的反应基团Q1，而在ω端包括一个靶分子，该化合物还包括符合以下式（1）或其盐的一个基团：该化合物也可以称为连接物-共轭物。本发明还涉及一种制备生物共轭物的方法，该方法包括将本发明中连接物-共轭物的反应基团Q1与生物分子的功能基团F1反应的步骤。本发明还涉及通过本发明方法获得的生物共轭物。在一个首选实施方式中，本发明涉及通过环加成反应制备生物共轭物的方法，例如（4+2）-环加成反应（例如Diels-Alder反应）或（3+2）-环加成反应（例如1,3-双极环加成）。
• [EN] MODIFIED ANTIBODY, ANTIBODY-CONJUGATE AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] ANTICORPS MODIFIÉ, ANTICORPS-CONJUGUÉ ET PROCÉDÉ DE PRÉPARATION ASSOCIÉ
  申请人：SYNAFFIX BV

  公开号：WO2014065661A1

  公开（公告）日：2014-05-01

  The present invention relates to an antibody comprising a GlcNAc-S(A)x substituent, wherein S(A)x is a sugar derivative comprising x functional groups A wherein A is independently selected from the group consisting of an azido group, a keto group and an alkynyl group and x is 1, 2, 3 or 4, wherein said GlcNAc-S(A)x substituent is bonded to the antibody via CI of the N-acetylglucosamine of said GlcNAc-S(A)x substituent, and wherein said N-acetylglucosamine is optionally fucosylated. The invention also relates to an antibody-conjugate, in particular to an antibody- conjugate according to the Formula (20) or (20b), wherein AB is an antibody, S is a sugar or a sugar derivative, D is a molecule of interest, and wherein said N- acetylglucosamine is optionally fucosylated (b is 0 or 1). The invention further relates to a process for the preparation of a modified antibody, to a process for the preparation of an antibody-conjugate, and to said antibody-conjugate for use as a medicament. In addition, the invention relates to a kit of parts comprising an azide-modified antibody and a linker-conjugate, wherein said linker-conjugate comprises a (hetero)cycloalkynyl group and one or more molecules of interest.

  本发明涉及一种包含GlcNAc-S(A)x取代基的抗体，其中S(A)x是一种包含x个功能基团A的糖衍生物，其中A是从包括偶氮基、酮基和炔基的组中独立选择的，x为1、2、3或4，其中所述的GlcNAc-S(A)x取代基通过所述的GlcNAc-S(A)x取代基的N-乙酰葡萄糖胺的CI与抗体结合，其中所述的N-乙酰葡萄糖胺可选择地被岩藻糖化。本发明还涉及一种抗体结合物，特别是根据式（20）或（20b）的抗体结合物，其中AB是一种抗体，S是一种糖或糖衍生物，D是一种感兴趣的分子，其中所述的N-乙酰葡萄糖胺可选择地被岩藻糖化（b为0或1）。本发明还涉及一种改性抗体的制备方法，一种抗体结合物的制备方法，以及用作药物的所述抗体结合物。此外，本发明还涉及一种部件套件，包括偶氮基修饰的抗体和连接物结合物，其中所述的连接物结合物包括（杂）环炔基团和一个或多个感兴趣的分子。
• [EN] PROCESS FOR THE MODIFICATION OF A GLYCOPROTEIN USING A ΒETA-(1,4)-N-ACETYLGALACTOSAMINYLTRANSFERASE OR A MUTANT THEREOF<br/>[FR] PROCÉDÉ POUR LA MODIFICATION D'UNE GLYCOPROTÉINE À L'AIDE D'UNE BÊTA-(1,4)-N-ACÉTYLGALACTOSAMINYL-TRANSFÉRASE OU D'UN MUTANT CORRESPONDANT
  申请人：SYNAFFIX BV

  公开号：WO2016022027A1

  公开（公告）日：2016-02-11

  The present invention relates to a process for the modification of a glycoprotein, using a β-(1,4)-N-acetylgalactosaminyltransferase or a mutant thereof.The process comprisesthe step of contacting a glycoprotein comprising a glycan comprising a terminal GlcNAc-moiety, in the presence of a β-(1,4)-N-acetylgalactosaminyl- transferase or a mutant thereof, with anon-natural sugar-derivative nucleotide.The non-natural sugar-derivative nucleotideis according to formula (3), wherein A is selected from the group consisting of -N3; -C(0)R3; -C=C-R4; -SH; -SC(0)R8; -SC(V)OR8, wherein V is O or S; -X wherein X is selected from the group consisting of F, CI, Br and I; -OS(0)2R5; an optionally substituted C2 - C24 alkyl group; an optionally substituted terminal C2 - C24 alkenyl group; and an optionally substituted terminal C3 - C24 allenyl group.

  本发明涉及一种修饰糖蛋白的过程，使用β-(1,4)-N-乙酰半乳糖氨基转移酶或其突变体。该过程包括以下步骤：在β-(1,4)-N-乙酰半乳糖氨基转移酶或其突变体存在下，将含有末端GlcNAc基团的糖蛋白与一种非天然糖衍生核苷酸接触。该非天然糖衍生核苷酸符合以下公式(3)，其中A选自-N3；-C(0)R3；-C=C-R4；-SH；-SC(0)R8；-SC(V)OR8，其中V为O或S；-X，其中X选自F、CI、Br和I；-OS(0)2R5；一个可选择取代的C2-C24烷基团；一个可选择取代的末端C2-C24烯基团；和一个可选择取代的末端C3-C24烯丙基团。
• [EN] PROCESS FOR THE CYCLOADDITION OF A HETERO(ARYL) 1,3-DIPOLE COMPOUND WITH A (HETERO)CYCLOALKYNE<br/>[FR] PROCÉDÉ DE CYCLOADDITION D'UN COMPOSÉ HÉTÉRO(ARYL) 1,3-DIPOLE AVEC UN (HÉTÉRO)CYCLOALKYNE
  申请人：STICHTING KATHOLIEKE UNIV

  公开号：WO2015112014A1

  公开（公告）日：2015-07-30

  The present invention relates to a process comprising the step of reacting a (hetero)aryl 1,3-dipole compound with a (hetero)cycloalkyne, wherein: a (hetero)aryl 1,3-dipole compound is defined as a compound comprising a 1,3-dipole functional group, wherein the 1,3-dipole functional group is bonded to a (hetero)aryl group, and wherein the (hetero)aryl 1,3-dipole compound is a (hetero)aryl azide or a (hetero)aryl diazo compound; wherein: (i) the (hetero)aryl group of the (hetero)aryl 1,3-dipole compound comprises one or more substituents having a positive value for the para-Hammett substituent constant σp and/or the meta-Hammett substituent constant σm, and/or (ii) the (hetero)aryl group of the (hetero)aryl 1,3-dipole compound is an electron-poor (hetero)aryl group, wherein an electron-poor (hetero)aryl group is: (ii-a) a (hetero)aryl group wherein the (hetero)aromatic ring system is bearing a positive charge, and/or (ii-b) a (hetero)aryl group wherein the ratio number of π-electrons present in the (hetero)aromatic ring system} : number of protons present in the nuclei of the (hetero)aromatic ring system} is lower than 0.167 for a 6-membered ring, or lower than 0.200 for a 5-membered ring; and wherein the (hetero)cycloalkyne is a (hetero)cyclooctyne or a (hetero)cyclononyne according to Formula (1): The invention also relates to the products obtainable by the process according to the invention.

  本发明涉及一种包括以下步骤的过程：将（杂）芳基1,3-二极化合物与（杂）环戊炔发生反应，其中：（杂）芳基1,3-二极化合物被定义为包含1,3-二极功能基团的化合物，其中1,3-二极功能基团与（杂）芳基团结合，而（杂）芳基1,3-二极化合物是（杂）芳基叠氮化物或（杂）芳基重氮化合物；其中：（i）（杂）芳基1,3-二极化合物的（杂）芳基团包括一个或多个对位Hammett取代常数σp和/或间位Hammett取代常数σm的正值取代基，和/或（ii）（杂）芳基1,3-二极化合物的（杂）芳基团是一个电子贫穷的（杂）芳基团，其中电子贫穷的（杂）芳基团是：（ii-a）一个（杂）芳基团，其中（杂）芳香环系统带有正电荷，和/或（ii-b）一个（杂）芳基团，其中比例（杂）芳香环系统中存在的π电子数}：（杂）芳香环系统中核内质子数}对于6元环小于0.167，或对于5元环小于0.200；其中（杂）环戊炔是根据式（1）的（杂）环辛炔或（杂）环壬炔；该发明还涉及根据该发明的过程获得的产品。