(GlcUA-GlcNAc)5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (GlcUA-GlcNAc)5
• 英文别名: GlcA(b1-3)GlcNAc(b1-4)GlcA(b1-3)GlcNAc(b1-4)GlcA(b1-3)GlcNAc(b1-4)GlcA(b1-3)GlcNAc(b1-4)GlcA(b1-3)GlcNAc；(2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₇₀H₁₀₇N₅O₅₆
• 分子量: 1914.62
• InChiKey: LSEDXWWDQCFYSU-ZRKAQMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -17.9
• 重原子数：
  131
• 可旋转键数：
  33
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  952
• 氢给体数：
  32
• 氢受体数：
  56

反应信息

• 作为反应物：
  描述：

  (GlcUA-GlcNAc)5 在 bovine testicular hyaluronidase, type 1-S 、 sodium chloride 作用下， 反应 24.0h， 以31.5%的产率得到hyaluronan tetrasaccharide
  参考文献：
  名称：

  Mechanism for the hydrolysis of hyaluronan oligosaccharides by bovine testicular hyaluronidase

  摘要：

  Synthetic hyaluronan oligosaccharides with defined structures and their pyridylaminated derivatives were used to investigate the mechanism of hydrolysis of hyaluronan by bovine testicular hyaluronidase. The products of the hydrolysis were analyzed by HPLC and ion‐spray mass spectroscopy (MS). It was confirmed that the minimum substrate for bovine testicular hyaluronidase is the hyaluronan hexasaccharide, even though it is a poor substrate that is barely cleaved, even on prolonged incubation. When hyaluronan octasaccharide was the substrate, increasing amounts of tetrasaccharide and hexasaccharide were produced with increasing time of incubation. Whereas disaccharide was not detectable in the reaction mixture by HPLC, MS analysis revealed trace amounts. The data suggest that the enzyme generates a disaccharide intermediate from hyaluronan oligosaccharide, the majority of which is transferred to the nonreducing ends of other oligosaccharides, only traces being released as free disaccharide. When hyaluronan octasaccharide, with an unsaturated glucuronic acid at the nonreducing end, was used as a substrate, only a tetrasaccharide was detected by HPLC. However, MS showed that the product was a mixture of equal amounts of two tetrasaccharides, one with and the other without the unsaturated glucuronic acid. This suggests that, in the case of substrates with a double bond at the nonreducing end, a tetrasaccharide is cleaved off instead of a disaccharide. The results of the experiments with pyridylaminated oligosaccharides were entirely consistent with these conclusions, and in addition showed the importance of the reducing end of the substrate for the enzyme to recognize the length of the saccharide.

  DOI：

  10.1111/j.1742-4658.2010.07600.x
• 作为产物：
  描述：

  sodium hyaluronate 在 ovine testicular hyaluronidase 、 sodium acetate 、 sodium chloride 作用下， 生成 hyaluronan tetrasaccharide 、 hyaluronan 、 (GlcUA-GlcNAc)5 、 hyaluronan octasaccharide
  参考文献：
  名称：

  透明质酸低聚糖的化学修饰差异调节透明质酸-透明质酸相互作用

  摘要：

  糖胺聚糖透明质酸 （HA） 是一种普遍存在的非硫酸化多糖，通过与 HA 结合蛋白 （HABP） 的相互作用介导多种生物学作用。大多数 HABP 属于 Link 模块超家族，包括主要的 HA 受体 CD44 和分泌蛋白 TSG-6，后者催化重链从 α 间抑制剂共价转移到 HA。CD44 （HABD_CD44） 和 TSG-6 （Link_TSG6） 的 HA 结合结构域 （HABD） 的结构已经确定，并且它们与 HA 的相互作用得到了广泛表征。结合机制不同，Link_TSG6主要通过离子和 CH−π 相互作用与 HA 相互作用，而 HABD_CD44 仅通过氢键和范德华力结合。在这里，我们利用这些差异来生成 HA 寡糖，在其还原端进行化学修饰，其特异性和差异性地结合这些目标 HABP。与未修饰的 HA6AN 相比，用 2-或 3-氨基苯甲酸 （HA6-2AA， HA6-3AA） 或 2-氨基-4-甲氧基苯甲酸

  DOI：

  10.1016/j.jbc.2024.107668

文献信息

• Mechanism for the hydrolysis of hyaluronan oligosaccharides by bovine testicular hyaluronidase
  作者：Ikuko Kakizaki、Nobuyuki Ibori、Kaoru Kojima、Masanori Yamaguchi、Masahiko Endo

  DOI：10.1111/j.1742-4658.2010.07600.x

  日期：2010.4

  Synthetic hyaluronan oligosaccharides with defined structures and their pyridylaminated derivatives were used to investigate the mechanism of hydrolysis of hyaluronan by bovine testicular hyaluronidase. The products of the hydrolysis were analyzed by HPLC and ion‐spray mass spectroscopy (MS). It was confirmed that the minimum substrate for bovine testicular hyaluronidase is the hyaluronan hexasaccharide, even though it is a poor substrate that is barely cleaved, even on prolonged incubation. When hyaluronan octasaccharide was the substrate, increasing amounts of tetrasaccharide and hexasaccharide were produced with increasing time of incubation. Whereas disaccharide was not detectable in the reaction mixture by HPLC, MS analysis revealed trace amounts. The data suggest that the enzyme generates a disaccharide intermediate from hyaluronan oligosaccharide, the majority of which is transferred to the nonreducing ends of other oligosaccharides, only traces being released as free disaccharide. When hyaluronan octasaccharide, with an unsaturated glucuronic acid at the nonreducing end, was used as a substrate, only a tetrasaccharide was detected by HPLC. However, MS showed that the product was a mixture of equal amounts of two tetrasaccharides, one with and the other without the unsaturated glucuronic acid. This suggests that, in the case of substrates with a double bond at the nonreducing end, a tetrasaccharide is cleaved off instead of a disaccharide. The results of the experiments with pyridylaminated oligosaccharides were entirely consistent with these conclusions, and in addition showed the importance of the reducing end of the substrate for the enzyme to recognize the length of the saccharide.