(S)-6-{(S)-2,6-Bis-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexanoylamino}-2-tert-butoxycarbonylamino-hexanoic acid | 865721-29-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (S)-6-{(S)-2,6-Bis-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexanoylamino}-2-tert-butoxycarbonylamino-hexanoic acid
• CAS: 865721-29-5
• 化学式: C₆₅H₁₁₀N₄O₁₃
• 分子量: 1155.61
• InChiKey: IAPDJJKUAZJNRS-ARYXLVHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.78
• 重原子数：
  82.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  284.31
• 氢给体数：
  11.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (S)-6-{(S)-2,6-Bis-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexanoylamino}-2-tert-butoxycarbonylamino-hexanoic acid 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Poly(choloyl)-Based Amphiphiles as Pore-Forming Agents:  Transport-Active Monomers by Design

  摘要：

  This paper describes the design and synthesis of a family of pore-forming amphiphiles. Two of these amphiphiles, which are derived from cholic acid, lysine, and p-phenylenediamine, can produce pores in lipid bilayers as individual molecules. In sharp contrast, analogous amphiphiles that do not contain a rigid 1,4-phenylenediamide moiety favor the formation of dimer-based pores. Kinetic evidence in support of monomer- and dimer-based pores has been obtained from Na+ transport measurements across bilayers made from 1-palmitoyl-2-oleoyl-2-sn-glycero-3-phosphocholine (POPC). Structure-activity studies that have been carried out with pore-forming, dimer-based amphiphiles have also revealed a significant activity dependence on their overall compactness. The practical potential of pore-forming amphiphiles with controllable supramolecular properties is briefly discussed.

  DOI：

  10.1021/ja053527q
• 作为产物：
  描述：

  cholic acid N-succinimidyl ester 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (S)-6-{(S)-2,6-Bis-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexanoylamino}-2-tert-butoxycarbonylamino-hexanoic acid
  参考文献：
  名称：

  Poly(choloyl)-Based Amphiphiles as Pore-Forming Agents:  Transport-Active Monomers by Design

  摘要：

  This paper describes the design and synthesis of a family of pore-forming amphiphiles. Two of these amphiphiles, which are derived from cholic acid, lysine, and p-phenylenediamine, can produce pores in lipid bilayers as individual molecules. In sharp contrast, analogous amphiphiles that do not contain a rigid 1,4-phenylenediamide moiety favor the formation of dimer-based pores. Kinetic evidence in support of monomer- and dimer-based pores has been obtained from Na+ transport measurements across bilayers made from 1-palmitoyl-2-oleoyl-2-sn-glycero-3-phosphocholine (POPC). Structure-activity studies that have been carried out with pore-forming, dimer-based amphiphiles have also revealed a significant activity dependence on their overall compactness. The practical potential of pore-forming amphiphiles with controllable supramolecular properties is briefly discussed.

  DOI：

  10.1021/ja053527q

文献信息

• [EN] SULFATED MOLECULAR UMBRELLAS CONTAINING 6-200 CHOLANIC ACID (DERIVATIVE) UNITS AS ANTI-HIV AND ANTI-HSV AGENTS<br/>[FR] PARAPLUIES MOLECULAIRES SULFATES EN TANT QU'AGENTS ANTI-VIH ET ANTI-VHS
  申请人：UNIV LEHIGH

  公开号：WO2006034369A3

  公开（公告）日：2006-06-01