6-Hydroxy-hexanoic acid ((S)-1-dihexadecylcarbamoyl-ethyl)-amide | 114307-60-7

• 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: 6-Hydroxy-hexanoic acid ((S)-1-dihexadecylcarbamoyl-ethyl)-amide
• 英文别名: N-[(2S)-1-(dihexadecylamino)-1-oxopropan-2-yl]-6-hydroxyhexanamide
• CAS: 114307-60-7
• 化学式: C₄₁H₈₂N₂O₃
• 分子量: 651.114
• InChiKey: NNXIPMICNNYDQL-KDXMTYKHSA-N

物化性质

• 沸点：
  744.2±45.0 °C(predicted)
• 密度：
  0.912±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.83
• 重原子数：
  46.0
• 可旋转键数：
  37.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  69.64
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-hexanoic acid ((S)-1-dihexadecylcarbamoyl-ethyl)-amide 在 四氯化锡 、 肼 作用下， 以 二氯甲烷 为溶剂， 生成 6-((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid ((S)-1-dihexadecylcarbamoyl-ethyl)-amide
  参考文献：
  名称：

  Preparation of Artificial Glycolipids and Their Aggregation Behavior in Aqueous Media

  摘要：

  N,N-Dihexadecyl-N-alpha-[6-(beta D-galactopyranosyl)hexanoyl]-L-alaninamide and N,N-dihexadecyl-N-alpha-[6-{(beta D-galactopyranosyl>(1 --> 4>O-(D-glucopyranosyl)}hexanoyl]-L-alaninamide, which have an amino acid residue interposed between a polar sugar moiety and a hydrophobic double-chain segment individually, were prepared and characterized as novel artificial glycolipids. Morphological studies by means of differential scanning calorimetry and dynamic light scattering as well as electron microscopy clarified that these lipids tend to form stable bilayer membranes by themselves in aqueous media. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01572-4
• 作为产物：
  描述：

  N,N-dihexadecyl-N^α-(t-butoxycarbonyl)-L-alaninamide 在 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 90.0h， 生成 6-Hydroxy-hexanoic acid ((S)-1-dihexadecylcarbamoyl-ethyl)-amide
  参考文献：
  名称：

  Preparation of Artificial Glycolipids and Their Aggregation Behavior in Aqueous Media

  摘要：

  N,N-Dihexadecyl-N-alpha-[6-(beta D-galactopyranosyl)hexanoyl]-L-alaninamide and N,N-dihexadecyl-N-alpha-[6-{(beta D-galactopyranosyl>(1 --> 4>O-(D-glucopyranosyl)}hexanoyl]-L-alaninamide, which have an amino acid residue interposed between a polar sugar moiety and a hydrophobic double-chain segment individually, were prepared and characterized as novel artificial glycolipids. Morphological studies by means of differential scanning calorimetry and dynamic light scattering as well as electron microscopy clarified that these lipids tend to form stable bilayer membranes by themselves in aqueous media. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01572-4

文献信息

• Aggregate Morphology of Peptide Lipids Having Hydroxyl Groups: Molecular Basis for Formation of Inverted Hexagonal, Inverted Cubic, Bilayer, and Micellar Phases
  作者：Yukito Murakami、Jun-ichi Kikuchi、Toshihiko Takaki、Katsuya Uchimura

  DOI：10.1246/bcsj.60.1469

  日期：1987.4

  Three types of peptide lipids having different numbers of hydroxyl groups in their head moieties, (HO)C5Ala2Cn, QC5Ala2Cn and Q2LysC5Ala2Cn (n=14, 16), were prepared, and their morphological behavior was investigated by various physical techniques: negative staining and freeze-fracture electron microscopy, low-angle X-ray diffraction, selected area electron diffraction, fluorescence polarization spectroscopy, and differential scanning calorimetry. QC5Ala2Cn, having four hydroxyl groups in the head moiety, underwent aggregation in the aqueous dispersion state to afford the nonbilayer phase, which was constituted with highly developed globular domains with face-centered cubic (CII) lattice, above the phase transition temperature (Tm). This CII phase was transformed into the bilayer one below Tm. On the other hand, Q2LysC5Ala2Cn, having eight hydroxyl groups in the head moiety, formed bilayer aggregates in a whole temperature range, above and below Tm. Deprotonation of the hydroxyl groups of QC5Ala2Cn and Q2LysC5Ala2Cn resulted in morphological changes to afford the bilayer and micellar phases, respectively. Two-component lipid systems composed of (HO)C5Ala2C14 and Q2LysC5Ala2C14 at appropriate molar ratios afforded the inverted hexagonal (HII) phase in the aqueous dispersion state; the first example of the HII phase formed with artificial double-chain amphiphiles. The aggregate morphology was discussed on the basis of the critical packing mode of lipid molecules.

  本研究制备了三种头部羟基数目不同的多肽脂质：(HO)C5Ala2Cn、QC5Ala2Cn和Q2LysC5Ala2Cn（n=14，16），并通过各种物理技术：负染色和冷冻断裂电子显微镜、低角度X射线衍射、选区电子衍射、荧光偏振光谱和差示扫描量热法研究了它们的形态行为。QC5Ala2Cn 的头部分子中含有四个羟基，在水分散状态下发生聚集，产生了非双层相，该相在相变温度（Tm）以上由高度发达的面心立方（CII）晶格的球状结构域构成。这种 CII 相在低于 Tm 时转变为双层相。另一方面，头分子中含有八个羟基的 Q2LysC5Ala2Cn 在整个温度范围内（高于和低于 Tm）都能形成双层聚集体。QC5Ala2Cn 和 Q2LysC5Ala2Cn 的羟基去质子化导致形态发生变化，分别形成双分子层和胶束相。由适当摩尔比的 (HO)C5Ala2C14 和 Q2LysC5Ala2C14 组成的双组分脂质系统在水分散状态下产生了倒六方（HII）相；这是人工双链两性化合物形成 HII 相的第一个实例。根据脂质分子的临界堆积模式对聚合体形态进行了讨论。