[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4R,5R)-3-acetyloxy-2-(acetyloxymethyl)-5-azido-6-fluorooxan-4-yl]oxyoxan-2-yl]methyl acetate | 667456-69-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4R,5R)-3-acetyloxy-2-(acetyloxymethyl)-5-azido-6-fluorooxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 667456-69-1
• 化学式: C₂₄H₃₂FN₃O₁₅
• 分子量: 621.528
• InChiKey: CXKWOUGKHPFWPY-RVJNQIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  200
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4R,5R)-3-acetyloxy-2-(acetyloxymethyl)-5-azido-6-fluorooxan-4-yl]oxyoxan-2-yl]methyl acetate 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 三乙胺 、 甲基肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 O-(β-D-galactopyranosyl)-(1->3')-2'-acetamido-2'-deoxy-α-D-galactopyranosyl hydroxylamine
  参考文献：
  名称：

  Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen

  摘要：

  The first synthesis of the tumor-associated alpha-aminooxy T-antigen 1, a relevant recognition motif for the direct construction of multitopic carbohydrate architecture of biological interest is described. The usefulness of this building block is emphasized with the efficient preparation through oxime ligation of a neoglycopeptide cluster, which is readily suitable for evaluating the role of multivalency in antigen presentation to the immune system from an anticancer vaccine perspective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.126
• 作为产物：
  描述：

  methyl 2-azido-2-deoxy-D-galactopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 对甲苯磺酸 、 溶剂黄146 、 乙二胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 硝基甲烷 、 二氯甲烷 为溶剂， 生成 [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4R,5R)-3-acetyloxy-2-(acetyloxymethyl)-5-azido-6-fluorooxan-4-yl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen

  摘要：

  The first synthesis of the tumor-associated alpha-aminooxy T-antigen 1, a relevant recognition motif for the direct construction of multitopic carbohydrate architecture of biological interest is described. The usefulness of this building block is emphasized with the efficient preparation through oxime ligation of a neoglycopeptide cluster, which is readily suitable for evaluating the role of multivalency in antigen presentation to the immune system from an anticancer vaccine perspective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.126

文献信息

• Solution-Phase Synthesis with Solid-State Workup of an <i>O</i>-Glycopeptide with a Cluster of Cancer-Related T Antigens
  作者：Ning Shao、Zhongwu Guo

  DOI：10.1021/ol0514193

  日期：2005.8.1

  An N-terminal glycopeptide of asialoglycophorin AM with three O-linked T antigens was prepared by "solution-phase synthesis with solid-state workup" using unprotected glycosyl amino acids as building blocks. For the glycopeptide assembly, all reactions were conducted in homogeneous NMP solutions, while the product of each reaction was readily isolated as solid precipitates upon addition of diethyl

  带有三个O-连接的T抗原的去唾液酸糖皮质激素AM的N-末端糖肽是通过“具有固相后处理的溶液相合成”，使用未保护的糖基氨基酸作为结构单元来制备的。对于糖肽组装，所有反应均在均相的NMP溶液中进行，而加入二乙醚后，每个反应的产物均易于分离为固体沉淀物。在构建模块的过程中，建立了一种鲁棒的方法来选择性地选择α-糖基化的Ser和Thr衍生物。[反应：看文字]
• Synthesis of multi-antigenic platforms as vaccine candidates against cancers
  作者：Michele Fiore、Baptiste Thomas、Vincent Duléry、Pascal Dumy、Olivier Renaudet

  DOI：10.1039/c2nj40972k

  日期：——

  Cancer cells are characterized by the presence of diverse antigens on their surface. The combination of these structures in a single molecule represents an attractive strategy to obtain vaccine candidates with improved immunological properties. Herein we report the synthesis of a mixture of heterotopic platforms bearing the Tn and TF carbohydrate antigens and an immunostimulating poliovirus peptide.

  癌细胞的特点是表面存在多种抗原。将这些结构组合在一个分子中，是获得具有更好免疫特性的候选疫苗的一种有吸引力的策略。在此，我们报告了带有Tn和TF碳水化合物抗原以及免疫刺激性脊髓灰质炎病毒肽的异位平台的混合物。
• Cyclic neoglycodecapeptides: how to increase their inhibitory activity and selectivity on lectin/toxin binding to a glycoprotein and cells
  作者：Sabine André、Olivier Renaudet、Isabelle Bossu、Pascal Dumy、Hans-Joachim Gabius

  DOI：10.1002/psc.1338

  日期：2011.6

  three adhesion/growth‐regulatory human lectins. They represent the different types of topological organization within the galectin family. The relative inhibitory activities of glycoclusters with the three ligands (galactose, lactose and the disaccharide of the Thomsen‐Friedenreich antigen) reflected the affinity of free carbohydrates, hereby excluding an impairment of binding activity by chemical derivatization

  蛋白质（凝集素/毒素）与聚糖的相互作用可能对临床有害，因此抑制剂的设计已成为目标。环状十肽适合作为碳水化合物衍生物的刚性载体。我们在本文中记录了在五种蛋白质（即有效的生物危害性植物凝集素，豆科植物凝集素和三种粘附/生长调节型人类凝集素）的情况下，与该载体共价连接的糖首基的生物活性。它们代表了半乳凝素家族中不同类型的拓扑组织。糖簇与三种配体（Thomsen-Friedenreich抗原的半乳糖，乳糖和二糖）的相对抑制活性反映了游离碳水化合物的亲和力，因此排除了化学衍生和结合对结合活性的损害。因此，头基团剪裁是优化基于环肽的糖簇的活性和选择性的一种途径。配体密度从四价到十六价的增加增加了第二条途径。植物毒素和串联重复型半乳凝素-4对这一参数变化特别敏感。战略性地将固相化验筛选与分析凝集素与不同系统中细胞的结合结合起来，揭示了不同糖簇的有效抑制作用，从而保护了细胞免受凝集素的结合。因此，环状新糖