4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside | 81119-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside
• 英文别名: 4-nitrophenyl 6-O-(N-acetyl-α-D-neuraminate-2-yl)-β-D-glucopyranoside；NeuAc(a2-6)Gal(b)-O-Ph(4-NO2)；(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxan-2-yl]methoxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 81119-31-5
• 化学式: C₂₃H₃₂N₂O₁₆
• 分子量: 592.511
• InChiKey: QAPJITZOKRVCEY-KAACSTQJSA-N

物化性质

• 沸点：
  1028.4±65.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  291
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside 在 Na₃PO₄ buffer 、 sodium acetate 、 十二烷基二甲基胺乙内酯 、 sodium chloride 、 calcium chloride 作用下， 生成 D-吡喃葡萄糖 、 对硝基苯酚 、 胞苷-5'-单磷酸-N-乙酰神经氨酸 、 4-硝基苯基-D-吡喃葡糖苷
  参考文献：
  名称：

  用于神经氨酸酶比色测定的键合特异性唾液酸底物的合成。

  摘要：

  通过将N-乙酰神经氨酸（Neup5Ac）与4-硝基苯基β-D-吡喃半乳糖苷的O-6和O-3与β-D-半乳糖苷-α-（-）连接起来，以高收率酶促合成了适合分析连接特异性的神经氨酸酶底物。 2 ---- 6）-唾液酸转移酶和β-D-半乳糖苷-α-（2 ---- 3）-唾液酸转移酶。通过使用这些底物，开发了一种方便的比色测定方法，用于确定细菌和病毒神经氨酸酶的连接特异性。将底物与病毒或细菌神经氨酸酶一起温育，然后用β-D-半乳糖苷酶处理，以将释放的4-硝基苯基β-D-半乳糖吡喃糖苷转化为4-硝基苯酚。释放的4-硝基苯酚的量等于从底物释放的Neup5Ac的量，因此可以测量神经氨酸酶活性。结果表明，细菌和病毒神经氨酸酶可以区分这两种化合物，使它们成为快速测定神经氨酸酶连接特异性的有用底物。

  DOI：

  10.1016/0008-6215(91)84090-2
• 作为产物：
  描述：

  p-nitrophenyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside
  参考文献：
  名称：

  Design and synthesis of a multivalent homing device for targeting to murine CD22

  摘要：

  CD22 is a cell-surface glycoprotein uniquely located on mature B-cells and B-cell derived tumour cells. Current evidence suggests that binding of endogenous ligands to CD22 leads to modulation of B-cell activation by antigen. Incidentally, however, B-cell activation may derail, and lead to an undesired immune response, for example in cases of allergy, rheumatoid arthritis and Crohn's disease. In this situation, synthetic high-affinity ligands for CD22 may be of therapeutic value as inhibitors of B-cell activation. Recent studies have revealed that natural ligands for CD22 contain the trisaccharide NeuAc alpha -2,6-Lac as the basic binding motif. In addition, it has been demonstrated that binding to CD22 is strongly enhanced by multivalent presentation of the basic binding motif (cluster effect). In this paper, the stepwise development of a novel multivalent high-affinity ligand for CD22 is described. In the first stage, a series of monovalent NeuAc alpha -2,6-Glc(Y)X type binding motifs was prepared, and their affinity for murine CD22 was monitored, to obtain more insight into the effect of separate structure elements on ligand recognition. In the second stage, we prepared a trivalent cluster, based on the monovalent motif that displayed the highest affinity for CD22, NeuAccc2,6-GlcNBzNO(2)OMe (7). This cluster, TRIS(NeuAc alpha -2,6-GlcNBzNO(2))(3) (52), displayed a more than 58-fold higher affinity for CD22 than the reference structure NeuAc alpha -2,6-LacOMe (10). To our knowledge, the cluster 52 is one of the most potent antagonists for CD22, yet synthesised. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00224-8

文献信息

• Design and synthesis of a multivalent homing device for targeting to murine CD22
  作者：Leo A.J.M. Sliedregt、Sabine M.W. van Rossenberg、Reshma Autar、A.Rob P.M. Valentijn、Gijs A. van der Marel、Jacques H. van Boom、Christina Piperi、P. Anton van der Merwe、Johan Kuiper、Theo J.C. van Berkel、Erik A.L. Biessen

  DOI：10.1016/s0968-0896(00)00224-8

  日期：2001.1

  CD22 is a cell-surface glycoprotein uniquely located on mature B-cells and B-cell derived tumour cells. Current evidence suggests that binding of endogenous ligands to CD22 leads to modulation of B-cell activation by antigen. Incidentally, however, B-cell activation may derail, and lead to an undesired immune response, for example in cases of allergy, rheumatoid arthritis and Crohn's disease. In this situation, synthetic high-affinity ligands for CD22 may be of therapeutic value as inhibitors of B-cell activation. Recent studies have revealed that natural ligands for CD22 contain the trisaccharide NeuAc alpha -2,6-Lac as the basic binding motif. In addition, it has been demonstrated that binding to CD22 is strongly enhanced by multivalent presentation of the basic binding motif (cluster effect). In this paper, the stepwise development of a novel multivalent high-affinity ligand for CD22 is described. In the first stage, a series of monovalent NeuAc alpha -2,6-Glc(Y)X type binding motifs was prepared, and their affinity for murine CD22 was monitored, to obtain more insight into the effect of separate structure elements on ligand recognition. In the second stage, we prepared a trivalent cluster, based on the monovalent motif that displayed the highest affinity for CD22, NeuAccc2,6-GlcNBzNO(2)OMe (7). This cluster, TRIS(NeuAc alpha -2,6-GlcNBzNO(2))(3) (52), displayed a more than 58-fold higher affinity for CD22 than the reference structure NeuAc alpha -2,6-LacOMe (10). To our knowledge, the cluster 52 is one of the most potent antagonists for CD22, yet synthesised. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of linkages-specific sialoside substrates for colorimetric assay of neuraminidases
  作者：Hisashi Kodama、Linda G. Baum、James C. Paulson

  DOI：10.1016/0008-6215(91)84090-2

  日期：1991.9

  bacterial and viral neuraminidases. The substrates are incubated with viral or bacterial neuraminidase and subsequently treated with beta-D-galactosidase to convert the liberated 4-nitrophenyl beta-D-galactopyranoside to 4-nitrophenol. The amount of liberated 4-nitrophenol is equivalent to the amount of Neup5Ac released from the substrate, thus allowing measurement of neuraminidase activity. The results

  通过将N-乙酰神经氨酸（Neup5Ac）与4-硝基苯基β-D-吡喃半乳糖苷的O-6和O-3与β-D-半乳糖苷-α-（-）连接起来，以高收率酶促合成了适合分析连接特异性的神经氨酸酶底物。 2 ---- 6）-唾液酸转移酶和β-D-半乳糖苷-α-（2 ---- 3）-唾液酸转移酶。通过使用这些底物，开发了一种方便的比色测定方法，用于确定细菌和病毒神经氨酸酶的连接特异性。将底物与病毒或细菌神经氨酸酶一起温育，然后用β-D-半乳糖苷酶处理，以将释放的4-硝基苯基β-D-半乳糖吡喃糖苷转化为4-硝基苯酚。释放的4-硝基苯酚的量等于从底物释放的Neup5Ac的量，因此可以测量神经氨酸酶活性。结果表明，细菌和病毒神经氨酸酶可以区分这两种化合物，使它们成为快速测定神经氨酸酶连接特异性的有用底物。