5-hexenyl 2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 864738-58-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-hexenyl 2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-hex-5-enoxyoxan-3-yl]oxy-3-hydroxyoxan-2-yl]methyl acetate
• CAS: 864738-58-9
• 化学式: C₃₀H₄₄O₁₇
• 分子量: 676.669
• InChiKey: RJICKQJYVLSFTG-KJRJSTJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  47
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,4,6-四-O-[(4-甲氧基苯基)甲基]-D-吡喃半乳糖基氟化物 、 5-hexenyl 2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 、 四氯化锡 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以95%的产率得到5-hexenyl 2,3,4,6-tetra-O-(p-methoxybenzyl)-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Assessment of Globotriose–Chitosan Conjugate, a Novel Inhibitor of Shiga Toxins Produced by Escherichia coli

  摘要：

  Shiga toxin (Stx)-producing Escherichia coli (STEC) causes diarrhea and colitis in humans that can develop into a life-threatening hemolytic uremic syndrome (HUS). Developing efficient means of controlling STEC diseases, for which no drugs or vaccines are currently available, remains a high priority. We report here the construction and development of chitosan conjugates bearing the Stx ligand trisaccharide globotriose to demonstrate their potential as STEC disease treatment agents. The synthesis was accomplished by grafting a globotriose derivative containing an aldehyde-functionalized aglycone to chitosan amino groups. The obtained globotriose-chitosan conjugate bound with high affinity to Stx and efficiently neutralized its toxicity on Vero cells. Moreover, Six levels in the gut of infected mice receiving oral doses of the conjugate were greatly diminished, enabling the mice to resist a fatal STEC challenge. The conjugate appears to function as a Stx adsorbent in the gut, preventing toxin entry into the bloodstream and consequent development of HUS. As such, the conjugate could act as a novel agent against STEC disease.

  DOI：

  10.1021/jm201570s
• 作为产物：
  描述：

  5-hexenyl β-lactoside 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-hexenyl 2,3,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Assessment of Globotriose–Chitosan Conjugate, a Novel Inhibitor of Shiga Toxins Produced by Escherichia coli

  摘要：

  Shiga toxin (Stx)-producing Escherichia coli (STEC) causes diarrhea and colitis in humans that can develop into a life-threatening hemolytic uremic syndrome (HUS). Developing efficient means of controlling STEC diseases, for which no drugs or vaccines are currently available, remains a high priority. We report here the construction and development of chitosan conjugates bearing the Stx ligand trisaccharide globotriose to demonstrate their potential as STEC disease treatment agents. The synthesis was accomplished by grafting a globotriose derivative containing an aldehyde-functionalized aglycone to chitosan amino groups. The obtained globotriose-chitosan conjugate bound with high affinity to Stx and efficiently neutralized its toxicity on Vero cells. Moreover, Six levels in the gut of infected mice receiving oral doses of the conjugate were greatly diminished, enabling the mice to resist a fatal STEC challenge. The conjugate appears to function as a Stx adsorbent in the gut, preventing toxin entry into the bloodstream and consequent development of HUS. As such, the conjugate could act as a novel agent against STEC disease.

  DOI：

  10.1021/jm201570s