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 | 79360-04-6

• 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: 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
• 英文别名: N2-{N2,N6-Bis[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosylthio)propionyl]-L-lysyl}-N6-[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosylthio)propionyl]-L-lysine；(2S)-2-[[(2S)-2,6-bis[3-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpropanoylamino]hexanoyl]amino]-6-[3-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpropanoylamino]hexanoic acid
• CAS: 79360-04-6；79390-77-5
• 化学式: C₆₃H₉₂N₄O₃₃S₃
• 分子量: 1529.63
• InChiKey: GLDMJIVVSAGNQR-MXRRZMMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  103
• 可旋转键数：
  53
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  573
• 氢给体数：
  5
• 氢受体数：
  36

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  L-lysyl-L-lysine dihydrochloride 、 p-nitrophenyl 3-(2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranosyl)propionate 在 三乙胺 、 三氟乙酸 作用下， 生成 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
  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：EP0063373B1

  公开（公告）日：1986-03-12