2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside | 221355-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside
• 英文别名: 2-azidoethyl-2,3,4,6-tetra-O-acetyl-N-acetyl-α-D-galactosamine；[(2R,3R,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(2-azidoethoxy)oxan-2-yl]methyl acetate
• CAS: 221355-51-7
• 化学式: C₁₆H₂₄N₄O₉
• 分子量: 416.388
• InChiKey: AZZGNJWMBPFQOP-LJIZCISZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 99.33h， 生成 (2R,2'R,3R,3'R,4R,4'R,5R,5'R,6S,6'S)-((13-(4-((tert-butoxycarbonyl)amino)butyl)-4,11,15,22-tetraoxo-3,10,13,16,23-pentaazapentacosane-1,25-diyl)bis(oxy))bis(5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-6,3,4-triyl) tetraacetate
  参考文献：
  名称：

  Cu(II)-Self-assembling bipyridyl-glycoclusters and dendrimers bearing the Tn-antigen cancer marker: syntheses and lectin binding properties

  摘要：

  Using the carbohydrate cancer marker, T-N-antigen (alpha-GalNAc-OR), covalently linked to a bipyridine core, square planar complexes were formed by self-assembly upon simple addition of Cu(11) sulfate. The required alpha-D-GalNAc-OR building block was constructed from 2-azidoethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (GlcNAc) by epimerization at C-4 of a suitably protected derivative followed by conventional modifications to provide 2-aminoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-galactopyranoside. The 2-aminoethyl aglycone was further elongated into a key monomer having an aminocaproic acid spacer together with their corresponding dimers using a double N-alkylation strategy of their N-bromoacetyl derivatives using mono-Boc-1,4-diaminobutane, respectively. The building blocks containing the bipyridyl dimers, having either a short or a long spacer arm, together with the tetramer built from the short spacer derivative were prepared in a convergent manner using 2,2'-bipyridine-4,4'-dicarboxylic acid chloride and the aminated sugar derivatives, respectively. Copper(II)-nucleated GalNAc derivatives containing four and eight residues were obtained from an aqueous solution of the bipyridyl derivatives. The relative inhibitory potencies of these glycodendrimers were evaluated against monomeric allyl alpha-D-GalNAc using a solid-phase competition assay with asialoglycophorin and horseradish peroxidase-labeled lectin Vicia villosa. The di- and tetra-valent bipyridyl clusters showed up to 87-fold increased inhibitory properties (IC50 7.14, 1.82, 4.09 muM, respectively) when compared to the monomer (IC50 158.3 muM) while the Cu(II)-complexes showed up to a 259-fold increase potencies (IC50 0.61 muM) with the octamer showing the highest affinity. However, when expressed on a per-saccharide basis, the tetramer Cu(II) nucleated derivative, possessing the longest inter-sugar distances showed the highest affinity (IC50 0.63 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00438-1
• 作为产物：
  描述：

  2-Chloroethyl 2-acetamido-2-deoxy-α-D-galactopyranoside 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  使用脂质 A 模拟物作为内置佐剂的 TF 候选癌症疫苗的设计、合成和生物活性评估

  摘要：

  本研究描述了五种基于 TF 的癌症候选疫苗的设计和合成，使用脂质 A 模拟物作为载体和内置佐剂。所有合成的缀合物在没有外部佐剂的情况下都能在小鼠体内引发强烈且一致的 TF 特异性免疫反应。随后在野生型和 TLR4 敲除 C57BL/6 小鼠中进行的免疫学研究表明，TLR4 的激活是合成的脂质 A 模拟物增加 TF 特异性免疫反应的主要原因。所有由这些缀合物诱导的抗血清都可以特异性识别、结合并诱导 TF 阳性癌细胞的裂解。此外，代表性结合物2和3能够有效减少体内肿瘤的生长，延长小鼠的生存时间，且疗效优于明矾佐剂的糖蛋白TF-CRM197。因此，脂质 A 模拟物可能成为开发具有自我辅助特性的新型碳水化合物疫苗载体的有前途的平台，用于治疗癌症。

  DOI：

  10.1021/acs.jmedchem.4c00042

文献信息

• Click glycoconjugation of per-azido- and alkynyl-functionalized β-peptides built from aspartic acid
  作者：Marielle Barra、Olivier Roy、Mounir Traïkia、Claude Taillefumier

  DOI：10.1039/b923275c

  日期：——

  Azide- and alkynyl-containing homo-β3-peptides, of up to six residues in length, were synthesised in solution from aspartic acid. Their subsequent conjugation with monosaccharides bearing an azide or a terminal alkyne function was efficiently achieved by copper-mediated cycloadditions leading to two novel families of small glycoclusters. These compounds represent ideal tools to explore carbohydrate-mediated multivalent interactions.

  以天冬氨酸为原料，在溶液中合成了长度达六个残基的含叠氮和炔基的同δ3-肽。随后，通过铜介导的环化反应，这些肽与带有叠氮或末端炔功能的单糖有效地结合在一起，形成了两个新型的小型糖簇家族。这些化合物是探索碳水化合物介导的多价相互作用的理想工具。
• Heteromultivalent Glycooligomers as Mimetics of Blood Group Antigens
  作者：Katharina S. Bücher、Patrick B. Konietzny、Nicole L. Snyder、Laura Hartmann

  DOI：10.1002/chem.201804505

  日期：——

  highly‐defined synthetic scaffold. Herein, we present a new strategy for the versatile assembly of heteromultivalent glycomacromolecules that contain different carbohydrate motifs in proximity within the side chains. A new building block suitable for the solid‐phase polymer synthesis of precision glycomacromolecules was developed with a branching point in the side chain that bears a free alkyne and a TIPS‐protected

  通过在高度定义的合成支架上显示多个聚糖表位，精密糖大分子已被证明是研究多价碳水化合物-凝集素相互作用的重要工具。在本文中，我们提出了一种新的策略，用于杂合多价糖大分子的多功能组装，该杂多价糖大分子在侧链内附近包含不同的碳水化合物基序。开发了一种适用于精密糖大分子固相聚合物合成的新构件，其侧链上的支化点带有一个游离炔和一个TIPS保护的炔部分，这使得随后的不同碳水化合物基序可以通过on-树脂铜介导的叠氮化物-炔烃环加成反应。应用这种综合策略，
• Carbohydrate Microarrays for Assaying Galactosyltransferase Activity
  作者：Sungjin Park、Injae Shin

  DOI：10.1021/ol070250l

  日期：2007.4.1

  Carbohydrate microarrays have been used recently for the rapid analysis of glycan-protein or glycan-cell interactions and for the detection of pathogens. As a demonstration of its significance and versatility, the microarray technology has been applied in this effort to assay glycosyltransferase activities. In addition, carbohydrate microarray based methods have been employed to quantitatively determine binding affinities between lectins and carbohydrates.
• Amphiphilicp-tert-Butylcalix[4]arene Scaffolds Containing Exposed Carbohydrate Dendrons
  作者：René Roy、Jin Mi Kim

  DOI：10.1002/(sici)1521-3773(19990201)38:3<369::aid-anie369>3.0.co;2-1

  日期：1999.2.1

  The best of both worlds. Amphiphilic hybrid molecules, in which water-exposed glycodendrons are attached to a hydrophobic p-tert-butylcalix[4]arene scaffold, display strong affinities for both carbohydrate-binding proteins and polystyrene surfaces (shown schematically). The molecules can form monolayers useful in bioanalytical devices.