N',N''-didodecyl-Nα-[3-(N'''-benzyloxycarbonyl)aminopropanoyl]-L-glutamide | 111682-03-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: N',N''-didodecyl-Nα-[3-(N'''-benzyloxycarbonyl)aminopropanoyl]-L-glutamide
• 英文别名: N',N"-didodecyl-Nα-[(3-(N'''-benzyloxycarbonyl)amino)propanoyl]-L-glutamide；benzyl N-[3-[[(2S)-1,5-bis(dodecylamino)-1,5-dioxopentan-2-yl]amino]-3-oxopropyl]carbamate
• CAS: 111682-03-2
• 化学式: C₄₀H₇₀N₄O₅
• 分子量: 687.02
• InChiKey: WTTUNZLHGMWLGV-BHVANESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  49
• 可旋转键数：
  33
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N',N''-didodecyl-Nα-[3-(N'''-benzyloxycarbonyl)aminopropanoyl]-L-glutamide 在 钯 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 (2S)-N,N'-didodecyl-2-[3-[(4-ethenylbenzoyl)amino]propanoylamino]pentanediamide
  参考文献：
  名称：

  Novel self-assembling organogelators by combination of a double chain-alkylated l-glutamide and a polymeric head groupElectronic supplementary information (ESI) available: table of gel-to-sol transition temperatures for G12-containing polymers; SEM of a xerogel from copoly-G12; temperature dependence of CD spectra of G12-vinyl and copoly-G12; experimental and characterisation data for G12-a, G12-b, G12-vinyl and copoly-G12. See http://www.rsc.org/suppdata/ob/b3/b305928f/

  摘要：

  这篇通讯介绍了一类新型自组装有机凝胶体，它由带有聚合物头基的双链烷基化 L-谷酰胺组成。

  DOI：

  10.1039/b305928f
• 作为产物：
  描述：

  十二烷基伯胺 在 钯 氰基磷酸二乙酯 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 N',N''-didodecyl-Nα-[3-(N'''-benzyloxycarbonyl)aminopropanoyl]-L-glutamide
  参考文献：
  名称：

  Novel self-assembling organogelators by combination of a double chain-alkylated l-glutamide and a polymeric head groupElectronic supplementary information (ESI) available: table of gel-to-sol transition temperatures for G12-containing polymers; SEM of a xerogel from copoly-G12; temperature dependence of CD spectra of G12-vinyl and copoly-G12; experimental and characterisation data for G12-a, G12-b, G12-vinyl and copoly-G12. See http://www.rsc.org/suppdata/ob/b3/b305928f/

  摘要：

  这篇通讯介绍了一类新型自组装有机凝胶体，它由带有聚合物头基的双链烷基化 L-谷酰胺组成。

  DOI：

  10.1039/b305928f

文献信息

• Functionalization of methyl orange using cationic peptide amphiphile: colorimetric discrimination between ATP and ADP at pH 2.0
  作者：Naoya Ryu、Hiroshi Hachisako

  DOI：10.1039/c0ob00437e

  日期：——

  A solvatochromic and non-fluorescent acid–base indicator, methyl orange (MO) was applied to colorimetric discrimination between adenosine triphosphate (ATP) and the corresponding diphosphate (ADP) at pH 2.0 in the presence of L-glutamic acid-derived cationic peptide amphiphile 1. This method is based on the fact that the amphiphile 1 can prevent MO from protonation even at pH 2.0. No similar colour change was observed when ADP was added instead of ATP under the same conditions. The effect of the molecular structure of several peptide amphiphiles and dyes was also investigated.

  在 pH 值为 2.0 时，在 L-谷氨酸衍生的阳离子肽亲和剂 1 的存在下，一种溶解变色且无荧光的酸碱指示剂甲基橙（MO）被用于比色法区分三磷酸腺苷（ATP）和相应的二磷酸腺苷（ADP）。这种方法的基础是，即使在 pH 值为 2.0 时，亲和剂 1 也能阻止 MO 发生质子化。在相同条件下，加入 ADP 而不是 ATP 时，没有观察到类似的颜色变化。此外，还研究了几种多肽两性化合物和染料的分子结构的影响。
• Amphiphilic molecular gels from ω-aminoalkylated l-glutamic acid derivatives with unique chiroptical properties
  作者：Yoshiko Kira、Yutaka Okazaki、Tsuyoshi Sawada、Makoto Takafuji、Hirotaka Ihara

  DOI：10.1007/s00726-010-0480-z

  日期：2010.7

  Self-assembling amphiphiles with unique chiroptical properties were derived from l-glutamic acid through omega-aminoalkylation and double long-chain alkylation. These amphiphiles can disperse in various solvents ranging from water to n-hexane. TEM and SEM observations indicate that the improvement in dispersity is induced by the formation of tubular and/or fibrillar aggregates with nanosized diameters, which makes these amphiphiles similar to aqueous lipid membrane systems. Spectroscopic observations, such as UV-visible and CD spectroscopies indicate that the aggregates are constructed on the basis of S- and R-chirally ordered structures through interamide interactions in water and organic media, respectively, and that these chiroptical properties can be controlled thermotropically and lyotropically. It is also reported that the chiral assemblies provide specific binding sites for achiral molecules and then induce chirality for the bonded molecules. Further, the applicability of the amphiphiles to template polymerization is discussed.