[2-(6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoylamino)-ethyl]-carbamic acid tert-butyl ester | 178912-24-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [2-(6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoylamino)-ethyl]-carbamic acid tert-butyl ester
• CAS: 178912-24-8
• 化学式: C₄₁H₆₈N₂O₉
• 分子量: 732.999
• InChiKey: SXXCLXDHTDBUNP-ZHLRVSPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  163.65
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [2-(6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoylamino)-ethyl]-carbamic acid tert-butyl ester 在 吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Efficient Transport of Aromatic Amino Acids by Sapphyrin-Lasalocid Conjugates

  摘要：

  The synthesis and characterization of several sapphyrin-lasalocid conjugates is reported. This family of receptors is capable of acting as efficient and selective carriers for aromatic alpha-amino acids, as judged from both U-tube and W-tube through-model-membrane transport experiments. The first member of this family, system 6, was found to display an inherent preference for phenylalanine > tryptophan > tyrosine. Further, L-amino acids were shown to be transported with greater efficiency than the corresponding D-enantiomers by this particular carrier. The high level of amino acid carrier capability displayed by receptor 6 in dichloromethane solutions correlates well with the results of equilibrium binding studies carried out using visible-spectroscopic titrations. These latter studies revealed that system 6 does display significant affinity for zwitterionic amino acids in this organic solvent. These binding studies, as well as a number of control experiments involving, inter alia, porphyrin-lasalocid conjugate 7, showed the importance of having both the sapphyrin and lasalocid subunits contained within the same overall receptor framework. The four other second-generation sapphyrin-lasalocid conjugates reported here (11-14) were also tested as carriers for the transport of Phe, Trp, and Tyr. It was found that the esterified systems 11 and 12 functioned well as amino acid carriers, while the free-acid compounds 13 and 14 did not. These latter conjugates, containing both carboxylic acid and sapphyrin subunits, presumably undergo self-assembly in organic solutions, a process that hampers their ability to act as effective carriers. In the case of the functioning systems 11 and 12, the configuration of the stereogenic phenylalanine appendages could be varied such that either the L- or D-antipodes of the aromatic amino acid substrates being studied were transported al a greater rate.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<159::aid-chem159>3.0.co;2-n
• 作为产物：
  描述：

  N-叔丁氧羰基-1,2-乙二胺 、 lasalocid sodium 在 吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以71%的产率得到[2-(6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoylamino)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Efficient Transport of Aromatic Amino Acids by Sapphyrin-Lasalocid Conjugates

  摘要：

  The synthesis and characterization of several sapphyrin-lasalocid conjugates is reported. This family of receptors is capable of acting as efficient and selective carriers for aromatic alpha-amino acids, as judged from both U-tube and W-tube through-model-membrane transport experiments. The first member of this family, system 6, was found to display an inherent preference for phenylalanine > tryptophan > tyrosine. Further, L-amino acids were shown to be transported with greater efficiency than the corresponding D-enantiomers by this particular carrier. The high level of amino acid carrier capability displayed by receptor 6 in dichloromethane solutions correlates well with the results of equilibrium binding studies carried out using visible-spectroscopic titrations. These latter studies revealed that system 6 does display significant affinity for zwitterionic amino acids in this organic solvent. These binding studies, as well as a number of control experiments involving, inter alia, porphyrin-lasalocid conjugate 7, showed the importance of having both the sapphyrin and lasalocid subunits contained within the same overall receptor framework. The four other second-generation sapphyrin-lasalocid conjugates reported here (11-14) were also tested as carriers for the transport of Phe, Trp, and Tyr. It was found that the esterified systems 11 and 12 functioned well as amino acid carriers, while the free-acid compounds 13 and 14 did not. These latter conjugates, containing both carboxylic acid and sapphyrin subunits, presumably undergo self-assembly in organic solutions, a process that hampers their ability to act as effective carriers. In the case of the functioning systems 11 and 12, the configuration of the stereogenic phenylalanine appendages could be varied such that either the L- or D-antipodes of the aromatic amino acid substrates being studied were transported al a greater rate.

  DOI：

  10.1002/(sici)1521-3765(199801)4:1<159::aid-chem159>3.0.co;2-n

文献信息

• Sapphyrin–lasalocid conjugate: a novel carrier for aromatic amino acid transport
  作者：Jonathan L. Sessler、Andrei Andrievsky

  DOI：10.1039/cc9960001119

  日期：——

  Sapphyrin, when connected covalently to lasalocid, acts as a selective carrier for the through-model-membrane transport of zwitterionic aromatic amino acids.