6-叠氮-6-脱氧-D-葡萄糖 | 20847-05-6

• 物质功能分类: 化学试剂 - 有机试剂 - 叠氮
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-叠氮-6-脱氧-D-葡萄糖
• 英文名称: 6-azido-6-deoxy-D-glucose
• 英文别名: (2R,3S,4R,5R)-6-azido-2,3,4,5-tetrahydroxyhexanal
• CAS: 20847-05-6
• 化学式: C₆H₁₁N₃O₅
• 分子量: 205.17
• InChiKey: HEYJIJWKSGKYTQ-JGWLITMVSA-N

物化性质

• 熔点：
  128-130 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 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：
  112
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  6-叠氮-6-脱氧-D-葡萄糖 在 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) 作用下， 以 环己酮 为溶剂， 反应 18.0h， 生成 6-azido-6-deoxy-D-glucono-1,5-lactone
  参考文献：
  名称：

  [EN] SYNTHESIS OF LACTONE DERIVATIVES AND THEIR USE IN THE MODIFICATION OF PROTEINS
  [FR] SYNTHÈSE DE DÉRIVÉS DE LACTONE ET LEUR UTILISATION DANS LA MODIFICATION DE PROTÉINES

  摘要：

  蛋白质的位点特异性修饰在生物技术应用中是可取的，例如生物制药、免疫疗法、疫苗，并且在化学生物学中也非常有用。葡萄糖酸化是一种非酶促的共价后翻译修饰，常见于带有N-末端His-标签的蛋白质上。我们合成了葡萄糖酸-1,5-内酯衍生物，包括用于选择性酰化的叠氮化衍生物。只需将衍生物与目标蛋白质混合在不同的温度、水溶液缓冲剂、辅料或复杂的细胞裂解液条件下，即可实现高产酰化。

  公开号：

  WO2021123229A1

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。
• Metabolic labeling and molecular enhancement of biological materials using bioorthogonal reactions
  申请人：The General Hospital Corporation

  公开号：US20170362266A1

  公开（公告）日：2017-12-21

  The present application provides methods of functionalizing an organ or tissue of a mammal by administering a nutrient (e.g., peracetylated N-azido galactosamine Ac4GalNAz) to the mammal or by culturing an organ or tissue in a bioreactor containing such nutrient. The present application also provides methods of selectively functionalizing extracellular matrix (ECM) of an organ or tissue of a mammal by administering a nutrient (e.g., peracetylated N-azido galactosamine Ac4GalNAz) to the mammal. In some aspects, the present application provides a decellularized scaffold of a mammalian organ or tissue comprising an extracellular matrix, wherein the extracellular matrix of the decellularized scaffold is functionalized with a chemical group that is reactive in a bioorthogonal chemical reaction, such as an azide chemical group. The present application also provides biological prosthetic mesh and mammalian organs and tissues for transplantation prepared according to the methods of the application.

  本申请提供了一种通过向哺乳动物投与营养物质（例如，乙酰化N-叠氮基半乳糖氨酸Ac4GalNAz）或在含有这种营养物质的生物反应器中培养器官或组织来功能化哺乳动物器官或组织的方法。本申请还提供了一种通过向哺乳动物投与营养物质（例如，乙酰化N-叠氮基半乳糖氨酸Ac4GalNAz）来选择性地功能化哺乳动物器官或组织的细胞外基质（ECM）的方法。在某些方面，本申请提供了哺乳动物器官或组织的脱细胞支架，其中脱细胞支架的细胞外基质被功能化为在生物正交化学反应中具有反应性的化学基团，例如叠氮基团。本申请还提供了根据本申请的方法制备的生物义肢网和哺乳动物器官和组织用于移植。
• GLYCOSYLTRANSFERASE REVERSIBILITY FOR SUGAR NUCLEOTIDE SYNTHESIS AND MICROSCALE SCANNING
  申请人：Thorson Jon S.

  公开号：US20130004979A1

  公开（公告）日：2013-01-03

  The present invention generally relates to materials and methods for exploiting glycosyltransferase reversibility for nucleotide diphosphate (NDP) sugar synthesis. The present invention provides engineered glycosyltransferase enzymes characterized by improved reaction reversibility and expanded sugar donor specificity as compared to corresponding non-mutated glycosyltransferase enzymes. Such reagents provide advantageous routes to NDP sugars for subsequent use in a variety of biomedical applications, including enzymatic and chemo-enzymatic glycorandomization.

  本发明一般涉及利用糖基转移酶可逆性合成核苷酸二磷酸（NDP）糖的材料和方法。本发明提供了改良反应可逆性并扩展糖供体特异性的工程糖基转移酶酶，与相应的非突变糖基转移酶酶相比，具有更好的反应可逆性和扩展的糖供体特异性。这些试剂提供了有利的NDP糖路线，用于随后在各种生物医学应用中使用，包括酶促和化学酶促糖随机化。
• 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。
• Chemoenzymatic Synthesis of Trehalose Analogs
  申请人：Central Michigan University

  公开号：US20150252402A1

  公开（公告）日：2015-09-10

  The present invention provides methods of synthesizing trehalose analogues; methods of detecting mycobacteria, and trehalose analogues.

  本发明提供了合成海藻糖类似物的方法；检测分枝杆菌的方法和海藻糖类似物。