N-[(2S,3S)-1-[4-[[2-[[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-bis[[2-[[1-[(2S,3S)-2-[[1-hydroxy-2-[[(2S)-2-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]amino]-3-methylbutanoyl]-[(4-methoxyphenyl)methyl]amino]-2-methylpropylidene]amino]-3-methylpentyl]triazol-4-yl]methoxy]acetyl]oxy]-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-oxoethoxy]methyl]triazol-1-yl]-3-methylpentan-2-yl]-2-[[(2S)-2-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]amino]-3-methylbutanoyl]-[(4-methoxyphenyl)methyl]amino]-2-methylpropanimidic acid | 1316672-98-6

• 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: N-[(2S,3S)-1-[4-[[2-[[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-bis[[2-[[1-[(2S,3S)-2-[[1-hydroxy-2-[[(2S)-2-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]amino]-3-methylbutanoyl]-[(4-methoxyphenyl)methyl]amino]-2-methylpropylidene]amino]-3-methylpentyl]triazol-4-yl]methoxy]acetyl]oxy]-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-oxoethoxy]methyl]triazol-1-yl]-3-methylpentan-2-yl]-2-[[(2S)-2-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]amino]-3-methylbutanoyl]-[(4-methoxyphenyl)methyl]amino]-2-methylpropanimidic acid
• CAS: 1316672-98-6
• 化学式: C₁₂₄H₁₉₂N₁₈O₂₆
• 分子量: 2350.99
• InChiKey: IGJPRBQJENXRFC-CVQVLOAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.2
• 重原子数：
  168
• 可旋转键数：
  68
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  516
• 氢给体数：
  6
• 氢受体数：
  32

反应信息

• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-L-valyl-N1-[(1S,2S)-1-(azidomethyl)-2-methylbutyl]-N2-(4-methoxybenzyl)-2-methylalaninamide 、 methyl (3α,5β,7α,12α)-3,7,12-tris{[(prop-2-yn-1-yloxy)acetyl]oxy}cholan-24-oate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以84%的产率得到N-[(2S,3S)-1-[4-[[2-[[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-bis[[2-[[1-[(2S,3S)-2-[[1-hydroxy-2-[[(2S)-2-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]amino]-3-methylbutanoyl]-[(4-methoxyphenyl)methyl]amino]-2-methylpropylidene]amino]-3-methylpentyl]triazol-4-yl]methoxy]acetyl]oxy]-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-oxoethoxy]methyl]triazol-1-yl]-3-methylpentan-2-yl]-2-[[(2S)-2-[[hydroxy-[(2-methylpropan-2-yl)oxy]methylidene]amino]-3-methylbutanoyl]-[(4-methoxyphenyl)methyl]amino]-2-methylpropanimidic acid
  参考文献：
  名称：

  Design and synthesis of bile acid–peptide conjugates linked via triazole moiety

  摘要：

  通过 Cu（I）催化的点击化学，描述了胆汁酸与肽的共轭。利用 Cu(I)-catalyzed 1,3-dipolar cycloaddition ("click "反应)，合成了基于胆酸、去氧胆酸和石胆酸衍生物的通过 1,2,3- 三唑分子连接的新型胆酸肽共轭物。研究表明，多达三个肽片段可以连接到一个中央甾体核心，从而形成复杂的三维多共轭结构，在生物化学、药物化学和配位化学中具有重要的应用价值。

  DOI：

  10.1039/c0ob01188f

文献信息

• Design and synthesis of bile acid–peptide conjugates linked via triazole moiety
  作者：Nadezhda V. Sokolova、Gennadij V. Latyshev、Nikolay V. Lukashev、Valentine G. Nenajdenko

  DOI：10.1039/c0ob01188f

  日期：——

  A conjugation of bile acids with peptidesviaCu(I)-catalyzed click chemistry has been described. Novel bile acid–peptide conjugates linked via a 1,2,3-triazole moiety based on cholic, deoxycholic and lithocholic acid derivatives were synthesized using Cu(I)-catalyzed 1,3-dipolar cycloaddition (“click” reaction). It was shown that up to three peptide fragments can be attached to a central steroid core, thus forming complex three-dimensional polyconjugate structures, which can find important applications in biochemistry, medicinal chemistry, and coordination chemistry.

  通过 Cu（I）催化的点击化学，描述了胆汁酸与肽的共轭。利用 Cu(I)-catalyzed 1,3-dipolar cycloaddition ("click "反应)，合成了基于胆酸、去氧胆酸和石胆酸衍生物的通过 1,2,3- 三唑分子连接的新型胆酸肽共轭物。研究表明，多达三个肽片段可以连接到一个中央甾体核心，从而形成复杂的三维多共轭结构，在生物化学、药物化学和配位化学中具有重要的应用价值。