β-D-glucopyranuronic acid-(1->3)-2-amino-2-deoxy-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranuronic acid-(1->3)-2-amino-2-deoxy-D-glucopyranose
• 英文别名: hyalobiuronic acid；GlcA(b1-3)GlcN；(2S,3S,4S,5R,6R)-6-[(3R,4R,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₁₂H₂₁NO₁₁
• 分子量: 355.299
• InChiKey: MMVCEIQLWBYBJB-DACPAPTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  212
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  甲醇 、 β-D-glucopyranuronic acid-(1->3)-2-amino-2-deoxy-D-glucopyranose 在 乙酰氯 作用下， 反应 64.0h， 以50%的产率得到(methyl β-D-glucopyranosyluronate)-(1->3)-2-amino-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  七（2,6-二-O-甲基）-β-环糊精与（2,4-二氯苯氧基）乙酸复合物的结构

  摘要：

  通过X射线衍射研究了由七（2,6-二-O-甲基）-β-环糊精与（2,4-二氯苯氧基）乙酸形成的配合物的结构。发现客体分子的二氯苯基部分位于主甲氧基基团区域的主体疏水腔之外，而氧乙酸链从主表面穿透腔。主体分子沿晶轴堆叠形成柱。在该柱的三个连续主体之间的空间中，容纳了一个客体分子。

  DOI：

  10.1016/s0008-6215(02)00114-3
• 作为产物：
  描述：

  hyaluronic acid 在 三氟乙酸 作用下， 反应 3.0h， 生成 2-deoxy-2-amino glucose 、 D-吡喃葡萄糖醛酸 、 β-D-glucopyranuronic acid-(1->3)-2-amino-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Acidolysis-based component mapping of glycosaminoglycans by reversed-phase high-performance liquid chromatography with off-line electrospray ionization–tandem mass spectrometry: Evidence and tags to distinguish different glycosaminoglycans

  摘要：

  Diverse monosaccharide analysis methods have been established for a long time, but few methods are available for a complete monosaccharide analysis of glycosaminoglycans (GAGS) and certain acidolysis-resistant components derived from GAGs. In this report, a reversed-phase high-performance liquid chromatography (RP-HPLC) method with pre-column 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization was established for a complete monosaccharide analysis of GAGs. Good separation of glucosamine/mannosamine (GIcN/ManN) and glucuronic acid/iduronic acid (GlcA/IdoA) was achieved. This method can also be applied to analyze the acidolysis-resistant disaccharides derived from GAGs, and the sequences of these disaccharides were confirmed by electrospray ionization-collision-induced dissociation-tandem mass spectrometry (ESI-CID-MS/MS). These unique disaccharides could be used as markers to distinguish heparin/heparan sulfate (HP/HS), chondroitin sulfate/dermatan sulfate (CS/DS), and hyaluronic acid (HA). (c) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2014.07.021

文献信息

• Acidolysis-based component mapping of glycosaminoglycans by reversed-phase high-performance liquid chromatography with off-line electrospray ionization–tandem mass spectrometry: Evidence and tags to distinguish different glycosaminoglycans
  作者：He Zhu、Xuan Chen、Xiao Zhang、Lili Liu、Dapeng Cong、Xia Zhao、Guangli Yu

  DOI：10.1016/j.ab.2014.07.021

  日期：2014.11

  Diverse monosaccharide analysis methods have been established for a long time, but few methods are available for a complete monosaccharide analysis of glycosaminoglycans (GAGS) and certain acidolysis-resistant components derived from GAGs. In this report, a reversed-phase high-performance liquid chromatography (RP-HPLC) method with pre-column 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization was established for a complete monosaccharide analysis of GAGs. Good separation of glucosamine/mannosamine (GIcN/ManN) and glucuronic acid/iduronic acid (GlcA/IdoA) was achieved. This method can also be applied to analyze the acidolysis-resistant disaccharides derived from GAGs, and the sequences of these disaccharides were confirmed by electrospray ionization-collision-induced dissociation-tandem mass spectrometry (ESI-CID-MS/MS). These unique disaccharides could be used as markers to distinguish heparin/heparan sulfate (HP/HS), chondroitin sulfate/dermatan sulfate (CS/DS), and hyaluronic acid (HA). (c) 2014 Elsevier Inc. All rights reserved.
• Structure of the complex of heptakis(2,6-di-O-methyl)-β-cyclodextrin with (2,4-dichlorophenoxy)acetic acid
  作者：Frantzeska Tsorteki、Dimitris Mentzafos

  DOI：10.1016/s0008-6215(02)00114-3

  日期：2002.7

  The structure of the complex formed by heptakis(2,6-di-O-methyl)-beta-cyclodextrin and (2,4-dichlorophenoxy)acetic acid was studied by X-ray diffraction. The dichlorophenyl moiety of the guest molecule was found outside the host hydrophobic cavity in the primary methoxy groups region whereas the oxyacetic acid chain penetrates the cavity from the primary face. The host molecules stacks along the a

  通过X射线衍射研究了由七（2,6-二-O-甲基）-β-环糊精与（2,4-二氯苯氧基）乙酸形成的配合物的结构。发现客体分子的二氯苯基部分位于主甲氧基基团区域的主体疏水腔之外，而氧乙酸链从主表面穿透腔。主体分子沿晶轴堆叠形成柱。在该柱的三个连续主体之间的空间中，容纳了一个客体分子。