6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide | 438194-50-4

• 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: 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide
• CAS: 438194-50-4
• 化学式: C₄₀H₅₀F₃N₃O₁₈S
• 分子量: 949.908
• InChiKey: IFMSFFGUTKWJKE-HPTPZDSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  65.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  265.61
• 氢给体数：
  1.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide 在 甲醇 、 sodium methylate 作用下， 反应 9.0h， 生成 6-(β-D-galactopyranosyl-(1->4)-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide
  参考文献：
  名称：

  Process for the modification of surface

  摘要：

  本发明涉及一种用于修改材料表面的过程，包括以下步骤：(a1) 光化学地将一个或多个不同的化合物按照公式固定在材料表面上，或者(a2) 光化学地将一个按照公式的化合物固定在材料表面上，然后将—ZH基团转化为—Z—X基团，其中变量的含义如索赔中所述；以及(b) 酶促地将一个或多个进一步的碳水化合物连接到根据步骤(a1)或(a2)获得的修改表面的X基团上。根据本发明的工艺获得的材料可用于制造生物医学设备，包括生物传感器。

  公开号：

  US06780980B1
• 作为产物：
  描述：

  6-己内酯 在 三氟化硼乙醚 、 氢溴酸 、 氯甲酸乙酯 、 三乙胺 、 硫脲 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.08h， 生成 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide
  参考文献：
  名称：

  Immobilisation on polystyrene of diazirine derivatives of mono- and disaccharides: biological activities of modified surfaces

  摘要：

  The potential of surface glycoengineering for biomaterials and biosensors originates from the importance of carbohydrate-protein interactions in biological systems. The strategy employed here utilises carbene generated by illumination of diazirine to achieve covalent bonding of carbohydrates. Here, we describe the synthesis of an aryl diazirine containing a disaccharide (lactose). Surface analysis techniques [X-ray photoelectron spectroscopy (XPS) and time of flight secondary ion mass spectroscopy (ToF-SIMS)] demonstrate its successful surface immobilisation on polystyrene (PS). Results are compared to those previously obtained with an aryl diazirine containing a monosaccharide (galactose). The biological activity of galactose- or lactose-modified PS samples is studied using rat hepatocytes, Allo A lectin and solid-phase semi-synthesis with alpha -2,6-sialyltransferase. Allo A shows some binding to galactose-modified PS but none to lactose-modified surfaces. Similar results are obtained with rat hepatocytes. In contrast, sialylation of lactose-modified PS is achieved but not with galactose-modified surfaces. The different responses indicate that the biological activity depends not only on the carbohydrate per se but also on the structure and length of the spacer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00172-9