(2S)-2-[[(2S)-2,6-二[3-[(2R,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]巯基丙酰氨基]己酰]氨基]-6-[3-[(2R,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]巯基丙酰氨基]己酸 | 79390-81-1

• 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
• 中文名称: (2S)-2-[[(2S)-2,6-二[3-[(2R,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]巯基丙酰氨基]己酰]氨基]-6-[3-[(2R,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]巯基丙酰氨基]己酸
• 英文名称: Man3Lys2
• 英文别名: N²-2,N⁶-bis<3-(α-D-mannopyranosylthio)propionyl>-L-lysine>-N⁶-<3-(α-D-mannopyranosylthio)propionyl>-L-lysine；N2-{N2,N6-bis[3-(α-D-mannopyranosylthio)propionyl]-L-lysyl}-N6-[3-(α-D-mannopyranosylthio)propionyl]-L-lysine；Trimannosyldilysine；(2S)-2-[[(2S)-2,6-bis[3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropanoylamino]hexanoyl]amino]-6-[3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropanoylamino]hexanoic acid
• CAS: 79390-81-1
• 化学式: C₃₉H₆₈N₄O₂₁S₃
• 分子量: 1025.18
• InChiKey: XNLMOLQNXJIGDH-DWRWFLLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  67
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  500
• 氢给体数：
  17
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  N²-2,N⁶-bis<3-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)thio>propionyl>-L-lysyl>-N⁶-<3-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)thio>propionyl>-L-lysine 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 以90%的产率得到(2S)-2-[[(2S)-2,6-二[3-[(2R,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]巯基丙酰氨基]己酰]氨基]-6-[3-[(2R,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]巯基丙酰氨基]己酸
  参考文献：
  名称：

  Cell-specific ligands for selective drug delivery to tissues and organs

  摘要：

  Various numbers of D-mannose residues have been attached via spacer arms to lysine, dilysine, and oligolysine backbones. These D-mannosyl peptide analogues were found to be potent competitive inhibitors of the uptake of 125I-labeled D-mannose-bovine serum albumin conjugate by rat alveolar macrophages. The inhibitory potency of these synthetic ligands increased with increasing number of carbohydrate moieties. The chirality of the peptide backbone did not appear to play a major role in binding, whereas variations of the length and linkage of the spacer arm notably affected the inhibitory activities. The saccharide specificity of the macrophage receptor was demonstrated by the inactivity of the corresponding D-galactosyl peptide analogues. The L-fucosyl peptide derivative was only weakly active. The trimannosyldilysine ligand (KI = 3.9 microM) and its analogues are potentially useful in selective delivery of therapeutic agents to macrophages.

  DOI：

  10.1021/jm00144a004

文献信息

• Cell-specific glycopeptide ligands
  申请人：Merck & Co., Inc.

  公开号：EP0063373A1

  公开（公告）日：1982-10-27

  Cell-specific ligands comprising conjugates of saccharides and amino acids or peptides are synthesized from amino acids such as ornithine, lysine, peptides such as dilysine, diornithine or oligolysine and selected saccharides having reactive functional groups protected by appropriate blocking groups. Such glycopeptides include e.g. N2-N2, N6-bis[3-(a-D-mannopyranosylthio)propionyl]-L-lysyl} -N6- [3-(a-D-mannopyranosylthiolpropionyl]-L-lysine (5). Those compounds are useful as tissue specific substances, which when coupled with bioactive materials through metabolizable or hydrolyzable linkages, deliver such bioactive materials to the selected site. In this manner, antiinflammatory drugs such as dexamethasone are linked through a metabolizable or hydrolyzable linkage and on administration to an animal suffering from inflammatory disease carries the drug to the site of inflammation for intracellular release.

  由糖和氨基酸或肽的共轭物组成的细胞特异性配体是由氨基酸（如鸟氨酸、赖氨酸）、肽（如二赖氨酸、二鸟氨酸或低聚赖氨酸）和具有活性官能团并受适当阻断基团保护的精选糖合成的。这类糖肽包括如 N2-N2，N6-双[3-（a-D-吡喃甘露糖硫基）丙酰基]-L-赖氨酸}-N6-[3-（a-D-吡喃甘露糖硫基）丙酰基]-L-赖氨酸（5）。这些化合物是有用的组织特异性物质，当通过可代谢或可水解的连接与生物活性物质结合时，可将这些生物活性物质输送到选定的部位。通过这种方式，地塞米松等抗炎药物通过可代谢或可水解连接，在给患有炎症疾病的动物用药时，可将药物带到炎症部位进行细胞内释放。
• Cell-specific ligands for selective drug delivery to tissues and organs
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、James C. Robbins、T. W. Doebber、T. Y. Shen

  DOI：10.1021/jm00144a004

  日期：1981.12

  Various numbers of D-mannose residues have been attached via spacer arms to lysine, dilysine, and oligolysine backbones. These D-mannosyl peptide analogues were found to be potent competitive inhibitors of the uptake of 125I-labeled D-mannose-bovine serum albumin conjugate by rat alveolar macrophages. The inhibitory potency of these synthetic ligands increased with increasing number of carbohydrate moieties. The chirality of the peptide backbone did not appear to play a major role in binding, whereas variations of the length and linkage of the spacer arm notably affected the inhibitory activities. The saccharide specificity of the macrophage receptor was demonstrated by the inactivity of the corresponding D-galactosyl peptide analogues. The L-fucosyl peptide derivative was only weakly active. The trimannosyldilysine ligand (KI = 3.9 microM) and its analogues are potentially useful in selective delivery of therapeutic agents to macrophages.