N-[2-[2-[2-[2-[2-[3-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropylamino]-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethyl]-11-[[11-[2-[2-[2-[2-[2-[3-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropylamino]-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethylamino]-11-oxoundecyl]disulfanyl]undecanamide | 1117751-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[2-[2-[2-[2-[2-[3-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropylamino]-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethyl]-11-[[11-[2-[2-[2-[2-[2-[3-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropylamino]-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethylamino]-11-oxoundecyl]disulfanyl]undecanamide
• CAS: 1117751-34-4
• 化学式: C₈₄H₁₅₄N₄O₄₄S₂
• 分子量: 1988.28
• InChiKey: AASGPUVIQVXINH-CVCYHDBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.8
• 重原子数：
  134
• 可旋转键数：
  75
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  756
• 氢给体数：
  24
• 氢受体数：
  46

反应信息

• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以87%的产率得到N-[2-[2-[2-[2-[2-[3-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropylamino]-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethyl]-11-[[11-[2-[2-[2-[2-[2-[3-[(2S,3S,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropylamino]-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethylamino]-11-oxoundecyl]disulfanyl]undecanamide
  参考文献：
  名称：

  Identification of trimannoside-recognizing peptide sequences from a T7 phage display screen using a QCM device

  摘要：

  Here, we report on the identification of trimannoside-recognizing peptide sequences from a T7 phage display screen using a quartz-crystal microbalance (QCM) device. A trimannoside derivative that can form a self-assembled monolayer (SAM) was synthesized and used for immobilization on the gold electrode surface of a QCM sensor chip. After six sets of one-cycle affinity selection, T7 phage particles displaying PSVGLFTH (8-mer) and SVGLGLGFSTVNCF (14-mer) were found to be enriched at a rate of 17/44, 9/44, respectively, suggesting that these peptides specifically recognize trimannoside. Binding checks using the respective single T7 phage and synthetic peptide also confirmed the specific binding of these sequences to the trimannoside-SAM. Subsequent analysis revealed that these sequences correspond to part of the primary amino acid sequence found in many mannose- or hexose- related proteins. Taken together, these results demonstrate the effectiveness of our T7 phage display environment for affinity selection of binding peptides. We anticipate this screening result will also be extremely useful in the development of inhibitors or drug delivery systems targeting polysaccharides as well as further investigations into the function of carbohydrates in vivo. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.004