(2S,3S,4S,5S)-6-azido-2,3,4,5,6-pentahydroxyhexanal

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5S)-6-azido-2,3,4,5,6-pentahydroxyhexanal
• 化学式: C6H11N3O6
• 分子量: 221.17
• InChiKey: YKVDKWKUEJQXNB-QTVWNMPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  133
• 氢给体数：
  5
• 氢受体数：
  8

文献信息

• [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。
• MODIFIED ANTIBODY, ANTIBODY-CONJUGATE AND PROCESS FOR THE PREPARATION THEREOF
  申请人：SYNAFFIX B.V.

  公开号：US20150258210A1

  公开（公告）日：2015-09-17

  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.

  本发明涉及一种抗体，包括GlcNAc-S（A）x取代基，其中S（A）x是一种糖衍生物，包括x个功能基团A，其中A独立地选自于由偶氮基团、酮基团和炔基团组成的群体，x为1、2、3或4，其中所述的GlcNAc-S（A）x取代基通过所述GlcNAc-S（A）x取代基的N-乙酰葡萄糖胺的CI键与抗体结合，其中所述的N-乙酰葡萄糖胺可选择性地被岩藻糖化。本发明还涉及一种抗体共轭物，特别是按照公式（20）或（20b）的抗体共轭物，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性地被岩藻糖化（b为0或1）。本发明还涉及一种改性抗体的制备方法，一种抗体共轭物的制备方法，以及用作药物的所述抗体共轭物。此外，本发明还涉及一种部件套件，包括偶氮化改性抗体和连接物共轭物，其中所述连接物共轭物包括一个（杂）环炔基团和一个或多个感兴趣的分子。
• MODIFIED GLYCOPROTEIN, PROTEIN-CONJUGATE AND PROCESS FOR THE PREPARATION THEREOF
  申请人：SYNAFFIX B.V.

  公开号：US20160250347A1

  公开（公告）日：2016-09-01

  Glycoproteins comprising a glycan of the formula (102) are disclosed; wherein b is 0 or 1; the GlcNAc residue optionally fucosylated; and Su(A) x is a sugar derivative comprising x functional groups A, wherein x is 1, 2, 3 or 4 and A is independently selected from the group consisting of an azido group, a keto group, an alkynyl group, a thiol group, a halogen, a sulfonyloxy group, a halogenated acetamido group, a mercaptoacetamido group and a sulfonylated hydroxyacetamido group. Protein-conjugates having glycoproteins according to the invention conjugated to a molecule of interest (e.g., an active substance) are also disclosed. Examples include modified antibodies, antibody-conjugates, and antibody-drug conjugates (ADCs). Processes for the preparation of the modified glycoproteins according to the invention and methods for the preparation of a protein-conjugate according to the invention are mentioned.

  本发明揭示了一种包含公式（102）的糖蛋白；其中b为0或1；GlcNAc残基可以选择性地被岩藻糖基化；Su（A）是一种糖衍生物，包括x个功能基团A，其中x为1、2、3或4，A独立地选择自由基组，包括偶氮基、酮基、炔基、硫醇基、卤素、磺酰氧基、卤代乙酰胺基、巯基乙酰胺基和磺酰化羟基乙酰胺基。 本发明还揭示了将本发明中的糖蛋白共轭到感兴趣的分子（例如，活性物质）上的蛋白质共轭物。例如，包括改性抗体、抗体共轭物和抗体药物共轭物（ADC）。还提及了制备本发明中改性糖蛋白的方法以及制备本发明中蛋白质共轭物的方法。
• METHOD OF PREPARATION OF 6-AZIDO-2,4-DIACETAMIDO-2,4,6-TRIDEOXY-D-MANNOSE
  申请人：Centre National de la Recherche Scientifique

  公开号：EP3170832A1

  公开（公告）日：2017-05-24

  The invention relates to a method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose. This method comprises the chemical reaction of compound of formula X: Wherein: R1 can be a C1 to C6 alkyl including methyl, ethyl, isopropyl; aryl including phenyl; each of these groups being substituted or not; and R2 can be a C1 to C6 alkyl including methyl, ethyl, isopropyl, tert-butyl, isobutyl; each of these groups being substituted or not; with a deprotecting reagent comprising a Lewis or Brönsted acid in a polar aprotic solvent, thereby obtaining a free C-1 OH group. The method can also start with the preparation from commercially available D-galactose pentaacetate, D-galactose tetraacetate or tetraacetyl D-galactosyl trichloroacetimidate. According to the invention the step of deprotecting the anomeric position avoids the use of cerium and allows the easy purification of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose.

  本发明涉及一种制备 6-叠氮-2,4-二乙酰氨基-2,4,6-三脱氧-D-甘露糖的方法。 该方法包括式 X 的化合物的化学反应： 其中 R1 可以是包括甲基、乙基、异丙基在内的 C1 至 C6 烷基；包括苯基在内的芳基；这些基团中的每个基团均可被取代或未被取代； R2 可以是 C1 至 C6 烷基，包括甲基、乙基、异丙基、叔丁基、异丁基；每个基团均被取代或未被取代； 在极性钝化溶剂中，用由路易斯酸或勃氏酸组成的脱保护试剂，从而获得游离的 C-1 OH 基团。 该方法也可以从市售的 D-半乳糖五乙酸酯、D-半乳糖四乙酸酯或 D-半乳糖基三氯乙酸亚氨酸四乙酸酯开始制备。 根据本发明，去保护同分异构体位置的步骤避免了铈的使用，并使 6-叠氮-2,4-二乙酰氨基-2,4,6-三脱氧-D-甘露糖易于纯化。
• Method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose
  申请人：Centre national de la recherche scientifique

  公开号：US10640526B2

  公开（公告）日：2020-05-05

  Disclosed is a method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose. This method includes the chemical reaction of compound of formula X: Wherein: R1 can be a C1 to C6 alkyl including methyl, ethyl, isopropyl; aryl including phenyl; each of these groups being substituted or not; and R2 can be a C1 to C6 alkyl including methyl, ethyl, isopropyl, tert-butyl, isobutyl; each of these groups being substituted or not; with a deprotecting reagent including a Lewis or Brönsted acid in a polar aprotic solvent, thereby obtaining a free C-1 OH group. The method can also start with the preparation from commercially available D-galactose pentaacetate, D-galactose tetraacetate or tetraacetyl D-galactosyl trichloroacetimidate. The step of deprotecting the anomeric position avoids the use of cerium and allows the easy purification of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose.

  本发明公开了一种制备 6-叠氮-2,4-二乙酰氨基-2,4,6-三脱氧-D-甘露糖的方法。该方法包括式 X 化合物的化学反应： 其中R1 可以是包括甲基、乙基、异丙基在内的 C1 至 C6 烷基；包括苯基在内的芳基；这些基团中的每个基团是否被取代；以及 R2 可以是包括甲基、乙基、异丙基、叔丁基、异丁基在内的 C1 至 C6 烷基；这些基团中的每个基团是否被取代。该方法也可以从市售的 D-半乳糖五乙酸酯、D-半乳糖四乙酸酯或 D-半乳糖基三氯乙酸亚氨酸四乙酸酯开始制备。去保护异构体位置的步骤避免了铈的使用，并使 6-叠氮-2,4-二乙酰氨基-2,4,6-三脱氧-D-甘露糖易于纯化。