6-aminohexyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside, acetic acid salt | 1351666-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-aminohexyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside, acetic acid salt
• 英文别名: 6-aminohexyl 2-acetamido-2-deoxy-3-O-α-L-fucopyranosyl-4-O-{3-O-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-β-D-galactopyranosyl}-β-D-glucopyranoside acetate
• CAS: 1351666-35-7
• 化学式: C₂H₄O₂*C₄₀H₇₁N₃O₂₅
• 分子量: 1054.06
• InChiKey: KLICLAYJJDZJML-RSRRBHHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.98
• 重原子数：
  72.0
• 可旋转键数：
  21.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  476.81
• 氢给体数：
  17.0
• 氢受体数：
  27.0

反应信息

• 作为产物：
  描述：

  6-azidohexyl 2-acetamido-4-O-{3-O-[2-acetamido-4,6-di-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranosyl]-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl}-6-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside 、 ammonium acetate 在 氨 、 sodium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以75%的产率得到6-aminohexyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside, acetic acid salt
  参考文献：
  名称：

  Aggregation of a Tetrasaccharide Acceptor Observed by NMR: Synthesis of Pentasaccharide Fragments of the Le^aLe^x Tumor-Associated Hexasaccharide Antigen

  摘要：

  We report the synthesis of a tetrasaccharide and two pentasaccharide fragments of the Le(a)Le(x) tumor-associated carbohydrate antigen alpha-L-Fuc-(1 -> 4)-[beta-d-Gal-(1 -> 3)]-beta-d-GlcNAc-(1 -> 3)-beta-d-Gal-(1 -> 4)-[alpha-l-Fuc-(1 -> 3)]-beta-d-GlcNAc-(1 -> OR). The choice of protecting groups permitted a one-step global deprotection (Na/NH3(l)). The protected chlorohexyl glycoside pentasaccharide was the precursor to the hexyl glycoside, to be used as a soluble inhibitor, and the aminohexyl glycoside analogue, to be conjugated to proteins for surface immobilization and immunization experiments. We observed that a linear tetrasaccharide that contained two N-acetylglucosamine residues and a free OH group gave two distinct sets of H-1 NMR signals when the data were acquired in deuterated chloroform. Data acquisition at variable concentrations and variable temperatures suggests that the second set of NMR signals results from aggregation of the tetrasaccharide driven by the formation of intermolecular H-bonds involving the NHAc. While the formation of intra- and intermolecular H-bonds involving N-acetylgucosamine residues has been reported in non-H-bonding solvents, this is, to our knowledge, the first time that these have lead to the appearance of two distinct sets of signals in the NMR spectra. This aggregation may explain the lack of reactivity observed when an attempt is made to glycosylate such an acceptor using non-H-bonding solvents such as dichloromethane.

  DOI：

  10.1021/acs.joc.5b00405

文献信息

• Unexpected structure of a C. difficile toxin A ligand necessitates an annotation correction in a popular screening library
  作者：Ping Zhang、Nahid Razi、Luiz Eugenio、Messele Fentabil、Elena N. Kitova、John S. Klassen、David R. Bundle、Kenneth K.-S. Ng、Chang-Chun Ling

  DOI：10.1039/c1cc15344g

  日期：——

  step of chemoenzymatic synthesis. When presented with a tetrasaccharide substrate containing both type I and type II disaccharide moieties, the enzyme generates a pentasaccharide in which the type II moiety is preferentially fucosylated. The unexpected product generated by FUT-III in this case highlights the importance of performing detailed structural analysis on products generated by enzymes.

  使用多种技术研究了功能糖业联盟中的五糖S259-1的结构。令人惊讶地，该结构不同于根据先前确定的化学酶促合成的最后步骤中使用的人岩藻糖基转移酶FUT-III的特异性所假定的结构。当与含有I型和II型二糖部分的四糖底物一起呈递时，该酶会生成五糖，其中II型部分优先被岩藻糖基化。在这种情况下，FUT-III产生的意外产物突出了对酶产生的产物进行详细结构分析的重要性。