methyl (3S,9S,15S,21S)-1-(8-((S)-2-((tert-butoxycarbonyl)amino)propanamido)pyren-1-yl)-3,6,6,9,12,12,15,18,18,21,24,24-dodecamethyl-1,4,7,10,13,16,19,22-octaoxo-2,5,8,11,14,17,20,23-octaazapentacosan-25-oate | 901780-61-8

• 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: methyl (3S,9S,15S,21S)-1-(8-((S)-2-((tert-butoxycarbonyl)amino)propanamido)pyren-1-yl)-3,6,6,9,12,12,15,18,18,21,24,24-dodecamethyl-1,4,7,10,13,16,19,22-octaoxo-2,5,8,11,14,17,20,23-octaazapentacosan-25-oate
• CAS: 901780-61-8
• 化学式: C₅₄H₇₄N₁₀O₁₃
• 分子量: 1071.24
• InChiKey: QQMXIWKHVQMPKZ-IIZANFQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  77.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  326.53
• 氢给体数：
  10.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl (3S,9S,15S,21S)-1-(8-((S)-2-((tert-butoxycarbonyl)amino)propanamido)pyren-1-yl)-3,6,6,9,12,12,15,18,18,21,24,24-dodecamethyl-1,4,7,10,13,16,19,22-octaoxo-2,5,8,11,14,17,20,23-octaazapentacosan-25-oate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 以57.4 mg的产率得到(3S,9S,15S,21S)-1-(8-((S)-2-((tert-butoxycarbonyl)amino)propanamido)pyren-1-yl)-3,6,6,9,12,12,15,18,18,21,24,24-dodecamethyl-1,4,7,10,13,16,19,22-octaoxo-2,5,8,11,14,17,20,23-octaazapentacosan-25-oic acid
  参考文献：
  名称：

  Helix Triangle:  Unique Peptide-Based Molecular Architecture

  摘要：

  We here report a unique cyclic peptide structure, "helix triangle", as a unique example of peptide-based molecular architecture. The cyclic peptide is designed to have a triangular shape in which three 9mer helical peptide units make the sides and three pyrene derivatives make the apexes. The helical peptide units are ideally linear, and the pyrene units are ideal 60 angular components. The yield of the cyclic peptide was relatively high despite its large cycle size. Absorption and fluorescence spectroscopy revealed that the three pyrene units do not interact with each other electronically, and circular dichroism spectroscopy indicated that the helical peptide units take 3(10)-helical conformation. Geometry optimization by the semi-empirical molecular orbital method gave a triangular structure with 3(10)-helices as the plausible molecular structure. To gain more information on the geometry and demonstrate one example of its self-assemblies, the monolayer of the cyclic peptide was prepared at the air/water interface, and its surface pressure-molecular area isotherm was studied. The isotherm indicated formation of a stable monolayer and suggested that the cyclic peptide actually takes the triangular structure predicted by the geometry optimization. The monolayer was then transferred onto a substrate and characterized by various methods. Ellipsometry and infrared reflection-absorption spectroscopy confirmed that the cyclic peptide has horizontal orientation to the surface in the monolayer. Furthermore, absorption and fluorescence spectroscopy showed that the isolated electronic properties of the pyrene units are intact even in a condensed state in the monolayer.

  DOI：

  10.1021/ja061989d
• 作为产物：
  描述：

  1-nitropyrene-8-carbonyl-(Ala-Aib)4-OMe 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 methyl (3S,9S,15S,21S)-1-(8-((S)-2-((tert-butoxycarbonyl)amino)propanamido)pyren-1-yl)-3,6,6,9,12,12,15,18,18,21,24,24-dodecamethyl-1,4,7,10,13,16,19,22-octaoxo-2,5,8,11,14,17,20,23-octaazapentacosan-25-oate
  参考文献：
  名称：

  Helix Triangle:  Unique Peptide-Based Molecular Architecture

  摘要：

  We here report a unique cyclic peptide structure, "helix triangle", as a unique example of peptide-based molecular architecture. The cyclic peptide is designed to have a triangular shape in which three 9mer helical peptide units make the sides and three pyrene derivatives make the apexes. The helical peptide units are ideally linear, and the pyrene units are ideal 60 angular components. The yield of the cyclic peptide was relatively high despite its large cycle size. Absorption and fluorescence spectroscopy revealed that the three pyrene units do not interact with each other electronically, and circular dichroism spectroscopy indicated that the helical peptide units take 3(10)-helical conformation. Geometry optimization by the semi-empirical molecular orbital method gave a triangular structure with 3(10)-helices as the plausible molecular structure. To gain more information on the geometry and demonstrate one example of its self-assemblies, the monolayer of the cyclic peptide was prepared at the air/water interface, and its surface pressure-molecular area isotherm was studied. The isotherm indicated formation of a stable monolayer and suggested that the cyclic peptide actually takes the triangular structure predicted by the geometry optimization. The monolayer was then transferred onto a substrate and characterized by various methods. Ellipsometry and infrared reflection-absorption spectroscopy confirmed that the cyclic peptide has horizontal orientation to the surface in the monolayer. Furthermore, absorption and fluorescence spectroscopy showed that the isolated electronic properties of the pyrene units are intact even in a condensed state in the monolayer.

  DOI：

  10.1021/ja061989d