Fmoc-Ser(Me4Glc)-OH | 1075171-78-6

• 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: Fmoc-Ser(Me4Glc)-OH
• CAS: 1075171-78-6
• 化学式: C₂₈H₃₅NO₁₀
• 分子量: 545.587
• InChiKey: WHIINHNRUVEACH-ZMGQXVQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131.01
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Rink resin 、 Fmoc-Ser(Me4Glc)-OH 、 Fmoc-甘氨酸 、 Fmoc-L-亮氨酸 、 乙酸酐 、 Fmoc-L-异亮氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-N-三苯甲基-L-天冬酰胺 、 Fmoc-N-三苯甲基-L-谷氨酰胺 在 哌啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Carbohydrate−π Interactions: What Are They Worth?

  摘要：

  Protein-carbohydrate interactions play an important role in many biologically important processes. The recognition is mediated by a number of noncovalent interactions, including an interaction between the a-face of the carbohydrate and the aromatic side chain of the protein. To elucidate this interaction, it has been studied in the context of a beta-hairpin in aqueous solution, in which the interaction can be investigated in the absence of other cooperative noncovalent interactions. In this beta-hairpin system, both the aromatic side chain and the carbohydrate were varied in an effort to gain greater insight into the driving force and magnitude of the carbohydrate-pi interaction. The magnitude of the interaction was found to vary from -0.5 to -0.8 kcal/mol, depending on the nature of the aromatic ring and the carbohydrate. Replacement of the aromatic ring with an aliphatic group resulted in a decrease in interaction energy to -0.1 kcal/mol, providing evidence for the contribution of CH-pi interactions to the driving force. These findings demonstrate the significance of carbohydrate-pi interactions within biological systems and also their utility as a molecular recognition element in designed systems.

  DOI：

  10.1021/ja803960x
• 作为产物：
  描述：

  Fmoc-L-丝氨酸 、 2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl bromide 在 silver trifluoromethanesulfonate 作用下， 反应 5.0h， 生成 Fmoc-Ser(Me4Glc)-OH
  参考文献：
  名称：

  Carbohydrate−π Interactions: What Are They Worth?

  摘要：

  Protein-carbohydrate interactions play an important role in many biologically important processes. The recognition is mediated by a number of noncovalent interactions, including an interaction between the a-face of the carbohydrate and the aromatic side chain of the protein. To elucidate this interaction, it has been studied in the context of a beta-hairpin in aqueous solution, in which the interaction can be investigated in the absence of other cooperative noncovalent interactions. In this beta-hairpin system, both the aromatic side chain and the carbohydrate were varied in an effort to gain greater insight into the driving force and magnitude of the carbohydrate-pi interaction. The magnitude of the interaction was found to vary from -0.5 to -0.8 kcal/mol, depending on the nature of the aromatic ring and the carbohydrate. Replacement of the aromatic ring with an aliphatic group resulted in a decrease in interaction energy to -0.1 kcal/mol, providing evidence for the contribution of CH-pi interactions to the driving force. These findings demonstrate the significance of carbohydrate-pi interactions within biological systems and also their utility as a molecular recognition element in designed systems.

  DOI：

  10.1021/ja803960x