N,N'-dipalmitoyl-(S)-lysinyl-(S)-alanyl-(S)-leucinyl-(S)-phenylalanyl-glycine[3-(β-D-galactopyranosyloxy)propyl]amide

• 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: N,N'-dipalmitoyl-(S)-lysinyl-(S)-alanyl-(S)-leucinyl-(S)-phenylalanyl-glycine[3-(β-D-galactopyranosyloxy)propyl]amide
• 英文别名: N-[(5S)-5-(hexadecanoylamino)-6-[[(2S)-1-[[(2S)-4-methyl-1-oxo-1-[[(2S)-1-oxo-1-[[2-oxo-2-[3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropylamino]ethyl]amino]-3-phenylpropan-2-yl]amino]pentan-2-yl]amino]-1-oxopropan-2-yl]amino]-6-oxohexyl]hexadecanamide
• 化学式: C₆₇H₁₁₉N₇O₁₃
• 分子量: 1230.72
• InChiKey: DHNDMZFZGANXSU-HFCVASNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  87
• 可旋转键数：
  53
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  303
• 氢给体数：
  11
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  3-aminopropyl β-D-galactopyranoside 、 N,N'-dipalmitoyl-(S)-lysinyl-(S)-alanyl-(S)-leucinyl-(S)-phenylalanyl-glycine 在 碳酸二异丙酯 、 HONB 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以13%的产率得到N,N'-dipalmitoyl-(S)-lysinyl-(S)-alanyl-(S)-leucinyl-(S)-phenylalanyl-glycine[3-(β-D-galactopyranosyloxy)propyl]amide
  参考文献：
  名称：

  Synthesis and Supramolecular Characterization of a Novel Class of Glycopyranosyl-Containing Amphiphiles

  摘要：

  A novel class of glycopeptidolipids is described, which potentially can be used as a novel antigen-delivery system. The compounds have been prepared by a combination of solid-supported and solution-based methods. The use of the orthogonally protected FmocLysDde derivative provided an opportunity to incorporate two different types lipids. It was found that the model compound 1 forms aggregates in aqueous media which can be described as rod or tubelike structures. The aggregates can be stabilized by topotactic photopolymerization. Studies on the structural analogues 2-5 revealed the effect of the carbohydrate, peptide, and lipid moiety on the aggregation properties. It is concluded that none of the structure elements can lay claim to be exclusively important for the formation of highly organized aggregates such as tubes, fibers, or helical ribbons from 1, but the presence of all of these structural elements afforded the most uniformly shaped extended structures.

  DOI：

  10.1021/jo991685s

文献信息

• Synthesis and Supramolecular Characterization of a Novel Class of Glycopyranosyl-Containing Amphiphiles
  作者：Frank Reichel、Annie M. Roelofsen、Hubertus P. M. Geurts、Sjerry J. van der Gaast、Martinus C. Feiters、Geert-Jan Boons

  DOI：10.1021/jo991685s

  日期：2000.6.1

  A novel class of glycopeptidolipids is described, which potentially can be used as a novel antigen-delivery system. The compounds have been prepared by a combination of solid-supported and solution-based methods. The use of the orthogonally protected FmocLysDde derivative provided an opportunity to incorporate two different types lipids. It was found that the model compound 1 forms aggregates in aqueous media which can be described as rod or tubelike structures. The aggregates can be stabilized by topotactic photopolymerization. Studies on the structural analogues 2-5 revealed the effect of the carbohydrate, peptide, and lipid moiety on the aggregation properties. It is concluded that none of the structure elements can lay claim to be exclusively important for the formation of highly organized aggregates such as tubes, fibers, or helical ribbons from 1, but the presence of all of these structural elements afforded the most uniformly shaped extended structures.