2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylacetic acid | 267235-22-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylacetic acid
• CAS: 267235-22-3
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: QMDHNPNDVMZVMN-HUHANWACSA-N

物化性质

• 沸点：
  492.1±35.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  151.73
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylacetic acid 、 Fmoc-Orn-OBn 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以85%的产率得到
  参考文献：
  名称：

  The Importance of Hydration for Inhibiting Ice Recrystallization with C-Linked Antifreeze Glycoproteins

  摘要：

  The role of hydration in modulating solution conformation, molecular recognition, and biological activity of oligosaccharides, proteins, and nucleotides is widely recognized but is often neglected when investigating many biological processes such as the mechanism by which biological antifreezes inhibit the growth of ice. We have investigated the relationship between carbohydrate configuration and recrystallization-inhibition (RI) activity in functional C-linked antifreeze glycoprotein (AFGP) analogues using a series of analogues 1-4. While analogues 1-4 did not show any thermal hysteresis (TH) activity, 1 did exhibit weak dynamic ice shaping indicating that this compound had the ability to interact with the ice lattice. The D-mannose and D-talose analogues (3 and 4, respectively) exhibited very weak RI activity with mean largest grain size values similar to phosphate buffered saline, the negative control. D-Glucose analogue 2 exhibited moderate RI activity while D-galactose analogue 1 was the most potent analogue with RI activity comparable to the native AFGP 8. These results suggest that the configuration of the carbohydrate moiety in C-linked AFGP analogues is extremely important and modulates recrystallization-inhibition activity. It seems likely that differences in hydration for each C-linked pyranose alter the compatibility of the carbohydrate moiety with the three-dimensional hydrogen-bonded network of supercooled bulk water. Consequently, the energy associated with transferring a water molecule to the ice lattice changes and can result in inhibition of ice growth. These results emphasize the importance of continued studies to further elucidate the role of hydration in antifreeze activity.

  DOI：

  10.1021/ja7103262
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene 在 sodium periodate 、 ruthenium(III) chloride trihydrate 、 水 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 3.0h， 以85%的产率得到2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylacetic acid
  参考文献：
  名称：

  通过糖基化-l-赖氨酸N-羧酸酐的活性聚合生成糖多肽

  摘要：

  描述了新的糖基化-L-赖氨酸-N-羧酸酐（糖-K NCA）单体的制备。这些单体使用 C 连接的糖和酰胺键连接到赖氨酸以提高稳定性而不牺牲生化特性。合成、纯化了三种糖基 K NCA，并发现它们使用过渡金属引发进行活性聚合。这些是糖基化 NCA 的首次活性聚合，用于制备定义明确的高分子量糖多肽以及阻断和统计糖多肽。这种方法解决了从 N-羧酸酐直接合成糖多肽中与单体合成、纯化和聚合相关的许多长期存在的问题，并提供了具有 100% 糖基化的多肽。

  DOI：

  10.1021/ja107425f