6-(β-D-galactopyranosyl-(1->4)-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide | 331442-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(β-D-galactopyranosyl-(1->4)-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide
• 英文别名: 5-carboxamidoypentyl N-[m-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-(β-D-galactopyranosyl)-(1→4)-1-thio-β-D-glucopyranoside；6-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanyl-N-[3-[3-(trifluoromethyl)diazirin-3-yl]phenyl]hexanamide
• CAS: 331442-99-0
• 化学式: C₂₆H₃₆F₃N₃O₁₁S
• 分子量: 655.647
• InChiKey: YABYGCJJAALADV-AYIBVMOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  248
• 氢给体数：
  8
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  6-巯基己酸 在 三氟化硼乙醚 、 sodium methylate 、 氯甲酸乙酯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.08h， 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：

  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

文献信息

• Process for the modification of surface
  申请人：Centre Suisse d'Electronique et de Microtechnique S.A.

  公开号：US06780980B1

  公开（公告）日：2004-08-24

  The present invention relates to a process for the modification of a material surface comprising the steps of (a1) photochemically fixing one or more different compounds of formula onto the material surface, or (a2) photochemically fixing a compound of formula onto the material surface and subsequently converting the —ZH groups to —Z—X moieties, wherein the variables each have the meanings as given in the claims; and (b) enzymatically attaching one or more further carbohydrates to the X radicals of the modified surface obtained according to stop (a1) or (a2). The materials obtainable by the process of the invention are useful, for example, for the manufacture of biomedical devices including biosensors.

  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。
• Immobilisation on polystyrene of diazirine derivatives of mono- and disaccharides: biological activities of modified surfaces
  作者：Y Chevolot、J Martins、N Milosevic、D Léonard、S Zeng、M Malissard、E.G Berger、P Maier、H.J Mathieu、D.H.G Crout、H Sigrist

  DOI：10.1016/s0968-0896(01)00172-9

  日期：2001.11

  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.