O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide | 246516-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide
• 英文别名: (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-azido-β-D-glucopyranoside
• CAS: 246516-71-2
• 化学式: C₃₈H₅₁N₃O₂₅
• 分子量: 949.828
• InChiKey: WOIUXBVWYAMLSM-CRCSEORLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.55
• 重原子数：
  66.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  357.91
• 氢给体数：
  0.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide 在 platinum(IV) oxide sodium azide 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~70.0 ℃ 、405.3 kPa 条件下， 反应 22.0h， 生成 N-[O-(β-D-galactopyranosyl)-(1->4)-1-β-D-glucopyranosyl]-5-aminopentamide
  参考文献：
  名称：

  Enhanced Inhibition of Human Anti-Gal Antibody Binding to Mammalian Cells by Synthetic α-Gal Epitope Polymers

  摘要：

  Neoglycopolymers of polyacrylamide backbone conjugated with varying densities of Gal alpha 1-3Gal beta 1-4Glc beta trisaccharide epitopes (alpha-Gal epitopes) were designed and synthesized to study the inhibition of the binding of human natural anti-Gal antibodies to either alpha-Gal-containing glycoproteins or alpha-Gal antigens on the surface of mammalian cells. An inhibition ELISA using mouse laminin and a flow cytometry assay using pig kidney cells (PK15) were established to determine the binding affinity of the synthesized polymers. In comparison to the alpha-Gal monomer (Gal alpha 1-3Gal beta 1-4GlcNHAc beta), the alpha-Gal polymers dramatically enhanced the inhibition of human anti-Gal antibodies (IgG, IgM, and IgA) binding to mouse laminin or mammalian cells. Increases of 7.8 x 10(3)- and 5.0 x 10(4) -fold in inhibitory potential of polymer 7C to IgA and IgM (with IC(50)s of 7.0 and 5.6 nM respectively) were observed over the monomer in inhibition ELISA. The results also indicated that binding enhancement of alpha-Gal polymers is greater for anti-Gal IgA and IgM than for IgG. Such amplified binding differences among the three anti-Gal isotypes can be utilized to selectively inhibit or remove a particular isotype of anti-Gal antibodies. Moreover, it was demonstrated through the flow cytometry assay that certain alpha-Gal polymers are effective in inhibition of anti-Gal antibody (in human serum) binding to pig kidney (PK15) cells. Thus, such synthetic carbohydrate polymers may find practical applications in cell xenotransplantations.

  DOI：

  10.1021/ja990219h
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-((2R,3R,4S,5R)-4,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-3-yloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 在 sodium azide 、 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以3.1 g的产率得到O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-β-D-glucopyranosyl azide
  参考文献：
  名称：

  用石英晶体微天平研究 α-Gal 碳水化合物抗原和蛋白质的相互作用

  摘要：

  近年来，石英晶体微量天平 (QCM) 已被探索作为光学生物传感器的替代品，用于检测生物试剂。 1 一些研究人员仍然对压电质量传感设备作为生物传感器的潜力持怀疑态度，2 因为液体中生物膜的物理特性复杂的。这种复杂性使得很难获得附加质量与频率输出变化之间的明确关系。一般而言，QCM 给出的响应表征固定在换能器表面的传感层与待检测分析物之间的结合事件。然而，通过 Sauerbrey 方程 3 用 QCM 响应估计的质量（即，Δf = -2Δmnf02/[A(μqρq)1/2]，其中 n 是泛音数，μq 是石英的剪切模量 (2.947 × 1011克/(cm•s2), ρq 是石英的密度 (2.648 g/cm3)，Δm/A 是面密度）取决于层流变特性。Sauerbrey 关系是通过假设附着的质量是刚性的并且与谐振器强耦合而推导出来的。例如，如果沉积的物质是粘弹性的，则它不适用。石英晶体谐振器对粘弹性敏感，4

  DOI：

  10.1021/ja035350a