(S)-2,6-Diamino-hexanoic acid (2-{2-[2-(2-{2,3-bis-[((Z)-octadec-9-enyl)oxy]-propoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-amide | 597533-74-9

• 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: (S)-2,6-Diamino-hexanoic acid (2-{2-[2-(2-{2,3-bis-[((Z)-octadec-9-enyl)oxy]-propoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-amide
• 英文别名: (2S)-2,6-diamino-N-[2-[2-[2-[2-[2,3-bis[(Z)-octadec-9-enoxy]propoxy]ethoxy]ethoxy]ethoxy]ethyl]hexanamide
• CAS: 597533-74-9
• 化学式: C₅₃H₁₀₅N₃O₇
• 分子量: 896.433
• InChiKey: CHOCMJMDPKWHPA-ZRNPVEGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  63
• 可旋转键数：
  54
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-2,6-Diamino-hexanoic acid (2-{2-[2-(2-{2,3-bis-[((Z)-octadec-9-enyl)oxy]-propoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-amide 、 (S)-2,6-Bis-(2-{2-[2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethoxy]-ethoxy}-acetylamino)-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2S)-N-[(5S)-6-[2-[2-[2-[2-[2,3-bis[(Z)-octadec-9-enoxy]propoxy]ethoxy]ethoxy]ethoxy]ethylimino]-6-hydroxy-5-[[(2S)-1-hydroxy-2,6-bis[[1-hydroxy-2-[2-[2-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylethoxy]ethoxy]ethylidene]amino]hexylidene]amino]hexyl]-2,6-bis[[1-hydroxy-2-[2-[2-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylethoxy]ethoxy]ethylidene]amino]hexanimidic acid
  参考文献：
  名称：

  Synthesis of an amphiphilic tetraantennary mannosyl conjugate and incorporation into liposome carriers

  摘要：

  We have synthesized a novel conjugate (Man(4)K(3)DOG) composed of a tetramannosyl head group connected, via a polyethylene glycol spacer, to a lipid moiety. This amphiphilic molecule was easily incorporated into the bilayers of liposomes. As expected from the clustering effect, such multivalent mannose residues when exposed on the surface of the vesicles showed much higher binding affinity for Concanavalin A than their monomannosyl analogue. Mannosylated liposomes prepared with the tetravalent antenna could be promising carriers for e.g., loading dendritic cells with antigens for vaccination purposes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00472-4
• 作为产物：
  描述：

  11-azide-1-{(methylsulfonyl)oxy}-3,6,9-trioxaundecane 在 水 、 sodium hydride 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-2,6-Diamino-hexanoic acid (2-{2-[2-(2-{2,3-bis-[((Z)-octadec-9-enyl)oxy]-propoxy}-ethoxy)-ethoxy]-ethoxy}-ethyl)-amide
  参考文献：
  名称：

  Synthesis of an amphiphilic tetraantennary mannosyl conjugate and incorporation into liposome carriers

  摘要：

  We have synthesized a novel conjugate (Man(4)K(3)DOG) composed of a tetramannosyl head group connected, via a polyethylene glycol spacer, to a lipid moiety. This amphiphilic molecule was easily incorporated into the bilayers of liposomes. As expected from the clustering effect, such multivalent mannose residues when exposed on the surface of the vesicles showed much higher binding affinity for Concanavalin A than their monomannosyl analogue. Mannosylated liposomes prepared with the tetravalent antenna could be promising carriers for e.g., loading dendritic cells with antigens for vaccination purposes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00472-4

文献信息

• Synthesis of an amphiphilic tetraantennary mannosyl conjugate and incorporation into liposome carriers
  作者：Socorro Espuelas、Philippe Haller、Francis Schuber、Benoı̂t Frisch

  DOI：10.1016/s0960-894x(03)00472-4

  日期：2003.8

  We have synthesized a novel conjugate (Man(4)K(3)DOG) composed of a tetramannosyl head group connected, via a polyethylene glycol spacer, to a lipid moiety. This amphiphilic molecule was easily incorporated into the bilayers of liposomes. As expected from the clustering effect, such multivalent mannose residues when exposed on the surface of the vesicles showed much higher binding affinity for Concanavalin A than their monomannosyl analogue. Mannosylated liposomes prepared with the tetravalent antenna could be promising carriers for e.g., loading dendritic cells with antigens for vaccination purposes. (C) 2003 Elsevier Ltd. All rights reserved.