O,O'-didodecyl-L-glutamate hydrochloride | 59441-30-4

• 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: O,O'-didodecyl-L-glutamate hydrochloride
• 英文别名: L-glutamic acid dilauryl ester hydrochloride；didodecyl (2S)-2-aminopentanedioate;hydron;chloride
• CAS: 59441-30-4
• 化学式: C₂₉H₅₇NO₄*ClH
• 分子量: 520.237
• InChiKey: YKLVAJZBWVTOGT-YCBFMBTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  35
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  78.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O,O'-didodecyl-L-glutamate hydrochloride 在 氰基磷酸二乙酯 、 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Regulation of β-Sheet Structures within Amyloid-Like β-Sheet Assemblage from Tripeptide Derivatives

  摘要：

  N-(11-Trimethylammonioundecanoyl)-O,O'-didodecyl tripeptide bromides and N-(11-trimethylammonioundecanyl)-O-dodecyl tripeptide bromides formed a parallel P-sheet structure when they aggregated in water and in CCl4. The parallel beta-sheet was distinguished from the antiparallel counterpart by Fourier transform infrared spectroscopy because the former lacks a weak band at about 1690 cm(-1) that is characteristic for the latter. The FT-IR spectra of the aggregate in CCl4 remained unchanged if the solution was diluted to 0.01 mM, condensed to dryness, or heated to 60 degrees C, and hence, the beta-sheet was easily formed and thermodynamically stable. The parallel beta-sheet was also possible to transform into an antiparallel beta-sheet, for example, by mixing with another tripeptide-containing amphiphile whose tripeptide part had an opposite direction. Transmission electron microscope (TEM) and atomic force microscope (AFM) pictures revealed that the aggregate in CCl4 is a bundle of small filaments whose diameters are 70-80 Angstrom. Developed interpeptide hydrogen bonding should be formed along the long axis of the filament. The, morphological structures and stable peptide arrangements of the present assemblages are similar to those of the amyloid fiber whose accumulation causes fatal diseases.

  DOI：

  10.1021/ja981363q
• 作为产物：
  描述：

  L-glutamic acid didodecyl ester p-toluenesulfonate 在 盐酸 作用下， 以 丙酮 为溶剂， 以27.45 g的产率得到O,O'-didodecyl-L-glutamate hydrochloride
  参考文献：
  名称：

  脂质包装的混合价配位聚合物中的近红外气相色谱

  摘要：

  具有脂质反离子的混合价铂配合物在近红外区域实现了可逆的气相色谱，有机蒸气从中排除结晶水会改变脂质分子的取向，从而将信息放大到一维配位结构和电子状态的变化。

  DOI：

  10.1039/d1cc06723k

文献信息

• Supramolecular architectures self-assembled using long chain alkylated spin crossover cobalt(<scp>ii</scp>) compounds
  作者：Ryohei Akiyoshi、Keita Kuroiwa、Saliu Alao Amolegbe、Manabu Nakaya、Ryo Ohtani、Masaaki Nakamura、Leonard F. Lindoy、Shinya Hayami

  DOI：10.1039/c7cc01501a

  日期：——

  Self-assembled hybrid supramolecular architectures formed between amphiphilic anions and long alkylated cationic cobalt(II) complexes of type [Co(Cn-terpy)2](C12-Glu)2 (n = 15–20) have been synthesized and characterized by TEM, PXRD and magnetic susceptibility measurements. The hybrids display wire or rolled sheet supramolecular arrangements with odd and even alkyl chain dependence, with the cobalt(II)

  两亲性阴离子与长型[Co（C n -terpy）2 ]（C 12 -Glu）2（n = 15-20）的长烷基化阳离子钴（II）配合物之间形成的自组装杂化超分子结构已被合成和表征通过TEM，PXRD和磁化率测量。杂种显示出具有奇数和偶数烷基链依赖性的金属丝或轧制薄板超分子排列，其中钴（II）中心表现出逐渐的自旋交叉行为。
• Lipid-Packaged Linear Iron(II) Triazole Complexes in Solution: Controlled Spin Conversion via Solvophobic Self-Assembly
  作者：Hiroyuki Matsukizono、Keita Kuroiwa、Nobuo Kimizuka

  DOI：10.1021/ja711355j

  日期：2008.4.1

  reversible spin conversion in toluene, with temperatures significantly higher (by 20-100 K) than the spin crossover temperatures observed in the crystalline states. This is accounted for in terms of increased metal-ligand interactions in organic media, which is caused by solvophobic compaction of charged coordination chains. In atomic force microscopy, developed nanowires are observed for low spin (LS) complexes

  线性 Fe(II) 1,2,4-三唑配合物与脂质反阴离子是新开发的。这些配合物在甲苯中显示出急剧和可逆的自旋转换，温度明显高于在结晶状态下观察到的自旋交叉温度（20-100 K）。这是由于有机介质中金属-配体相互作用增加的原因，这是由带电配位链的疏溶剂压实引起的。在原子力显微镜中，可以观察到低自旋 (LS) 复合物的发达纳米线。另一方面，对于高自旋 (HS) 复合物，可以看到碎片化的纳米结构，这表明溶液中的自旋转换是由自组装过程控制的。因此，带电配位链的脂质包装为通过疏溶剂自组装改善和调节其功能提供了强有力的手段。
• Silva, Monica de Lourdes de Araujo; Felicio, Emanoel de Castro Antunes, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 7, p. 645 - 652
  作者：Silva, Monica de Lourdes de Araujo、Felicio, Emanoel de Castro Antunes

  DOI：——

  日期：——
• Self-assembly of bilayers from double-chain fluorocarbon amphiphiles in aprotic organic solvents: thermodynamic origin and generalization of the bilayer assembly
  作者：Yuichi Ishikawa、Hiroaki Kuwahara、Toyoki Kunitake

  DOI：10.1021/ja00092a008

  日期：1994.6

  We designed new fluorocarbon amphiphiles, 3-7, that undergo spontaneous bilayer formation in organic media. They are comprized of double fluorocarbon chains and a single oleyl chain as solvophobic and solovophilic moieties, respectively. These two molecular modules were linked through the chiral L-glutamate residue. When dispersed in chlorocyclohexane or benzene, these amphiphiles formed stable bilayer assemblies that gave rise to morphologies such as tubes, tapes, rods, and particles as confirmed by electron microscopy. These dispersions showed bilayer/monomer phase transitions as inferred by differential scanning calorimetry. This phase transition was accompanied by changes of the helical pitch of the fluorocarbon conformation and of intermolecular hydrogen bonding among the glutamate moiety. From the surface tension analysis of adsorbed monolayers at the air/liquid interface, we concluded that the bilayer formation in bulk chlorocyclohexane was driven by the enthalpic change. Limited miscibilities between fluorocarbon chains and hydrocarbon solvents produced the main enthalpic driving force of the molecular association, and the hydrogen bonding and van der Waals force of the aromatic moieties served as secondary driving forces. The molar fraction at CMC (critical membrane or micelle concentration), which reflects instability of aggregates, was greater than those of aqueous bilayers (below 10(-7)) but smaller than those of aqueous micelles (above 10(-4)). The chromophoric bilayers 6 (Phe-Ole) and 7 (Azo-Ole) showed large molecular ellipticities of 10(5)-10(6) deg.cm(2).dmol(-1) in their CD spectra, Molecular ordering in the novel bilayers was not inferior to those of conventional aqueous bilayers, although their bilayer stability does not surpass that of aqueous bilayers.
• Okahata, Yoshio; Niikura, Ken-ichi; Ijiro, Kuniharu, Journal of the Chemical Society. Perkin transactions I, 1995, # 7, p. 919 - 926
  作者：Okahata, Yoshio、Niikura, Ken-ichi、Ijiro, Kuniharu

  DOI：——

  日期：——