methyl 2-azido-2-deoxy-β-D-galactopyranoside | 87376-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-azido-2-deoxy-β-D-galactopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4-diol；Methyl 2-azido-2-deoxy-beta-D-galactopyranoside；(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-methoxyoxane-3,4-diol
• CAS: 87376-50-9
• 化学式: C₇H₁₃N₃O₅
• 分子量: 219.197
• InChiKey: QYZPIZZUWJKSTF-XUUWZHRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-2-deoxy-β-D-galactopyranoside 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 、 sodium iodide 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸酐 、 N,N-二甲基甲酰胺 、 甲苯 、 苯甲醇 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 94.5h， 生成 N-((3S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl)acetamide
  参考文献：
  名称：

  Integrating thin film microfluidics in developing a concise synthesis of DGJNAc: A potent inhibitor of α-N-acetylgalctosaminidases

  摘要：

  A simple synthesis, which utilizes a thin film microfluidic reactor for a problematic step, of a potent inhibitor of alpha-N-acetylhexosaminidases, DGJNAc, has been developed.

  DOI：

  10.1016/j.bmcl.2018.10.015
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 在 sodium methylate 、 silver carbonate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 methyl 2-azido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  拥挤的双磷酸化摩根氏菌两性离子三糖重复单元的全合成

  摘要：

  两性离子多糖 (ZPS) 通过主要组织相容性复合体 II 类呈递激活 T 细胞依赖性免疫反应。在此，我们报告了摩根氏菌 ZPS 重复单元的首次合成，作为合成新型 ZPS 材料的有利工具。重复单元包含一个 1,2-顺式-α-糖苷键；有问题的 1,2-反式半乳糖苷键，Gal-β(1→3)-GalNAc；和磷酸甘油和磷酸胆碱残基，它们以前没有被观察到作为同一寡糖上的官能团。成功的第三代方法利用了磷酸甘油功能化受体的一流糖基化。为了安装磷酸胆碱单元，合成了一种高效的磷酸胆碱供体。

  DOI：

  10.1021/jacs.9b06830

文献信息

• [EN] TARGETED BIFUNCTIONAL DEGRADERS<br/>[FR] AGENTS DE DÉGRADATION BIFONCTIONNELS CIBLÉS
  申请人：UNIV YALE

  公开号：WO2021072269A1

  公开（公告）日：2021-04-15

  The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.

  本发明在一个方面提供了可以用来促进或增强降解某些循环蛋白的双功能化合物。在另一个方面，本发明提供了可以用来促进或增强降解某些自身抗体的双功能化合物。在某些实施方式中，治疗或管理疾病和/或疾病需要降解、去除或减少受试者体内循环蛋白或自身抗体的浓度。因此，在某些实施方式中，将本发明的化合物给予受试者可去除或减少循环蛋白或自身抗体的循环浓度，从而治疗、改善或预防疾病和/或疾病。在某些实施方式中，循环蛋白是TNF。
• [EN] ENGINEERED ANTIBODIES AS MOLECULAR DEGRADERS THROUGH CELLULAR RECEPTORS<br/>[FR] ANTICORPS CONÇUS COMME AGENTS DE DÉGRADATION MOLÉCULAIRE PAR L'INTERMÉDIAIRE DE RÉCEPTEURS CELLULAIRES
  申请人：UNIV YALE

  公开号：WO2021072246A1

  公开（公告）日：2021-04-15

  The present disclosure provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In certain embodiments, the circulating protein mediates a disease and/or disorder in a subject, and treatment or management of the disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein in the subject. Thus, in certain embodiments, administration of a compound of the disclosure to the subject removes or reduces the circulation concentration of the circulating protein, thus treating, ameliorating, or preventing the disease and/or disorder.

  本公开提供了一种双功能化合物，可用于促进或增强特定循环蛋白的降解。在某些实施例中，循环蛋白在受试者中介导疾病和/或紊乱，治疗或管理该疾病和/或紊乱需要降解、去除或减少受试者中循环蛋白的浓度。因此，在某些实施例中，将本公开的化合物给予受试者可去除或减少循环蛋白的循环浓度，从而治疗、改善或预防疾病和/或紊乱。
• SUBSTITUTED-6,8-DIOXABICYCLO[3.2.1]OCTANE-2,3-DIOL COMPOUNDS AS TARGETING AGENTS OF ASGPR
  申请人：Pfizer Inc.

  公开号：US20150329555A1

  公开（公告）日：2015-11-19

  Compounds of Formula (A) are described herein and the uses thereof for the treatment of diseases, conditions and/or disorders mediated by pharmaceutical compositions and the uses thereof as asialoglycoprotein receptor (ASGPR) targeting agents.

  公式（A）的化合物在本文件中被描述，以及它们用于治疗由药物组合物介导的疾病、状况和/或紊乱的使用，以及它们作为阿索糖蛋白受体（ASGPR）靶向剂的使用。
• [EN] ASGPR-BINDING COMPOUNDS FOR THE DEGRADATION OF EXTRACELLULAR PROTEINS<br/>[FR] COMPOSÉS SE LIANT À L'ASGPR POUR LA DÉGRADATION DE PROTÉINES EXTRACELLULAIRES
  申请人：AVILAR THERAPEUTICS INC

  公开号：WO2021155317A1

  公开（公告）日：2021-08-05

  Compounds and compositions that have an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein are described.

  描述了将一个与外细胞蛋白结合配体结合的阿斯利康糖蛋白受体（ASGPR）结合配体的化合物和组合物，用于选择性降解体内靶外细胞蛋白以治疗由外细胞蛋白介导的疾病。
• Synthesis of disaccharide congeners of the <i>Trichinella spiralis</i> glycan and binding site mapping of two monoclonal antibodies
  作者：Ping Zhang、Judith Appleton、Chang-Chun Ling、David R Bundle

  DOI：10.1139/v02-117

  日期：2002.8.1

  The tetrasaccharide epitope, β-D-Tyvp(1[Formula: see text]3)β-D-GalNAcp(1[Formula: see text]4)[α-L-Fucp(1[Formula: see text]3)]β-D-GlcNAcp (1) is the major constituent of the N-glycan expressed on the cell surface of the parasite Trichinella spiralis. Two monoclonal antibodies (Mabs 9D4 and 18H1) that protect rats against infection by T. spiralis bind the terminal disaccharide epitope β-D-Tyvp(1[Formula: see text]3)β-D-GalNAcp conjugated to BSA. The syntheses of disaccharide congeners containing mono-deoxy, mono-methyl, as well as modifications to replace the acetamido group are reported. These target disaccharides were assayed for binding to the protective MAbs. For each antibody different clusters of three hydroxyl groups, that include C-2 and C-4 of tyvelose and for 18H1, the GalNAc acetamido group, provide the key polar interactions with the antibody binding sites. Mapping of the sites by functional group replacement revealed a similar pattern of recognition for the dideoxyhexose by the two MAbs while each recognizes distinct surfaces of the GalNAc residue. Consequently although both antibodies bury the 4-OH of tyvelose, the principal contact surface occurs on opposite sides of the 3,6-dideoxyhexose.Key words: β-tyveloside, 3,6-dideoxy-D-arabino-hexose, Trichinella carbohydrate antigen, antibody mapping, Trichinella spiralis, N-glycans, molecular recognition of carbohydrates, antigen topology, functional group replacement.

  四糖基表位，β-D-Tyvp（1 [Formula：see text] 3）β-D-GalNAcp（1 [Formula：see text] 4）[α-L-Fucp（1 [Formula：see text] 3）]β-D-GlcNAcp（1）是寄生虫旋毛虫细胞表面表达的N-糖基的主要成分。两种单克隆抗体（Mabs 9D4和18H1）能保护大鼠免受旋毛虫感染，它们结合到与BSA结合的终端二糖基表位β-D-Tyvp（1 [Formula：see text] 3）β-D-GalNAcp。报道了含有单脱氧，单甲基以及替换乙酰胺基团的修饰的二糖类似物的合成。对这些靶向二糖的结合进行了保护MAbs的测定。对于每种抗体，包括tyvelose的C-2和C-4以及18H1的GalNAc乙酰胺基团的三个羟基团簇提供了与抗体结合位点的关键极性相互作用。通过功能团替换的映射表明，两种MAbs对于二脱氧己糖的识别模式相似，而每种MAbs都识别GalNAc残基的不同表面。因此，尽管两种抗体都掩埋了tyvelose的4-OH，但主要接触表面出现在3,6-二脱氧己糖的相反侧。 关键词：β-tyveloside，3,6-二脱氧-D-阿拉伯糖，旋毛虫糖原抗原，抗体映射，旋毛虫，N-糖基，碳水化合物的分子识别，抗原拓扑，功能团替换。