| 1258506-84-1

• CAS: 1258506-84-1
• 化学式: C₃₀H₃₈N₆O₁₀S₄
• 分子量: 770.93
• InChiKey: NUYQVVSBQPIBGV-BTNSXGMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  50.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  283.5
• 氢给体数：
  10.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  H-Cys-Tyr-Cys(Acm)-S-S-Cys(Acm)-Tyr-Cys-OH 在 盐酸 、 碘 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以22.0 mg的产率得到
  参考文献：
  名称：

  Peptide-Based Carbohydrate Receptors

  摘要：

  AbstractA broad spectrum of physiological processes is mediated by highly specific noncovalent interactions of carbohydrates and proteins. In a recent communication we identified several cyclic hexapeptides in a dynamic combinatorial library that interact selectively with carbohydrates with high binding constants in water. Herein, we report a detailed investigation of the noncovalent interaction of two cyclic hexapeptides (Cys‐His‐Cys (which we call HisHis) and Cys‐Tyr‐Cys (which we call TyrTyr)) with a selection of monosaccharides and disaccharides in aqueous solution. The parallel and antiparallel isomers of HisHis or TyrTyr were synthesized separately, and their interaction with monosaccharides and disaccharides in aqueous solution was studied by isothermal titration calorimetry, NMR spectroscopic titrations, and circular dichroism spectroscopy. From these measurements, we identified particularly stable complexes (Ka>1000 M−1) of the parallel isomer of HisHis with N‐acetylneuraminic acid and with methyl‐α‐D‐galactopyranoside as well as of both isomers of TyrTyr with trehalose. To gain further insight into the structure of the peptide–carbohydrate complexes, structure prediction was performed using quantum chemical methods. The calculations confirm the selectivity observed in the experiments and indicate the formation of multiple intermolecular hydrogen bonds in the most stable complexes.

  DOI：

  10.1002/chem.201303777