N-十六酰基-D-苯丙氨酸 | 1009313-87-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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
• 中文名称: N-十六酰基-D-苯丙氨酸
• 英文名称: N-palmitoyl-L-phenylalanine
• 英文别名: N-palmitoyl-D-phenylalanine；N-Hexadecanoyl-D-phenylalanine；(2R)-2-(hexadecanoylamino)-3-phenylpropanoic acid
• CAS: 1009313-87-4
• 化学式: C₂₅H₄₁NO₃
• 分子量: 403.605
• InChiKey: BAHIJPSQSKWCJX-HSZRJFAPSA-N

物化性质

• 沸点：
  580.3±43.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  D-苯丙氨酸甲酯 在 盐酸 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-十六酰基-D-苯丙氨酸
  参考文献：
  名称：

  从两亲性肽中寻找受生物启发的水凝胶：用于稳定释放抗癌药的纳米粒子稳定剂的模板†

  摘要：

  由于其在生物医学领域中的多样化应用，在过去的几十年中，有效的刺激响应水凝胶的发展迅速扩展。根据这种漂移，我们旨在调节一系列具有通式Me-（CH 2）14 -CO-NH-CH（X）-COOH的两亲肽类似物，其中X = CH 2 Ph在水凝胶仪I中（L -Phe）和II（D -Phe）且X = CH 2 Ph（OH）在水凝剂III（L-Tyr），无论其在C端中心的配置如何，在室温下都具有极好的固定水的能力，最小水凝胶I-III的胶凝浓度为0.04％/ 0.05％/ 0.02％w / v。。为了验证该阈值浓度差异，我们进行了计算分析，证明了水凝胶化剂I和III的侧链与两亲物和芳香环的亚甲基单元保持高度平面的能力，从而通过范德华力和pi促进了良好的对应关系。 –pi堆叠。因此，水凝剂I和III在比水凝剂II优越的有序组织中自组装。此外，光谱和显微镜实验表明，水凝胶化剂在超分子水平上表现出β-折叠构

  DOI：

  10.1039/c9nj01763a

文献信息

• STEREOSELECTIVE DEACYLATION OF LONG-CHAIN<i>p</i>-NITROPHENYL<i>N</i>-ACYLPHENYLALANATES BY PALMITOYL-L-HISTIDINE IN A BILAYER SYSTEM
  作者：Ryuichi Ueoka、Yoko Matsumoto、Yashushi Ninomiya、Yoshiharu Nakagawa、Kazuhiro Inoue、Katsutoshi Ohkubo

  DOI：10.1246/cl.1981.785

  日期：1981.6.5

  In the stereoselective deacylation of H–[CH2]n-1–CONHCH(CH2Ph)CO2–C6H4NO2-p (n=10 and 16), the bilayer catalytic systems of palmitoyl-l-histidine and double-chain surfactants ([CmH2m+1]2N[CH3]2Br; m=12 and 14) offered the relatively higher enantiomer rate ratios (kcatL⁄kcatD=3.7–5.6) as compared with those (kcatL⁄kcatD=3.5–3.6) obtanined with the comicellar system of palmitoyl-l-histidine and octadecyltrimethylammonium chloride.

  在H–[CH2]n-1–CONHCH(CH2Ph)CO2–C6H4NO2-p的立体选择性去酰化反应中（n=10和16），棕榈酰-l-组氨酸和双链表面活性剂（[CmH2m+1]2N[CH3]2Br; m=12和14）形成的双层催化系统相比于棕榈酰-l-组氨酸和氯化十八烷基三甲基铵的共微胞系统（kcatL⁄kcatD=3.5–3.6），提供了相对更高的对映体反应速率比（kcatL⁄kcatD=3.7–5.6）。
• Enantioselective Hydrolysis of<i>N</i>-Acyl Amino Acid Esters by Tripeptide-type L-Histidine Derivative in a Bilayer Vesicular System
  作者：Katsutoshi Ohkubo、Hitoshi Ishida、Kazuhiro Yamaki、Masahiko Kawata

  DOI：10.1246/cl.1991.1723

  日期：1991.10

  Peculiar enantioselective hydrolysis of N-acyl amino acid esters was found in the bilayer vesicular systems containing the tripeptide-type histidine derivative, Z-L-Leu-L-His-L-Leu. The enantioselectivity for the hydrolysis of long chain N-acyl phenylalanine p-nitrophenyl ester, C16-Phe-PNP, appeared in the binding process and was governed by an entropy factor.

  在含有三肽型组氨酸衍生物 ZL-Leu-L-His-L-Leu 的双层囊泡系统中发现了 N-酰基氨基酸酯的特殊对映选择性水解。长链 N-酰基苯丙氨酸对硝基苯酯 C16-Phe-PNP 水解的对映选择性出现在结合过程中，并受熵因子控制。
• Anionic surfactant templated chiral nanospheres and their enantioselective adsorption
  作者：Bin Di、Lifei Cheng、Qiuling Jiang、Mengxiang Su、Weiqiang Hao

  DOI：10.1039/c3nj00219e

  日期：——

  Monodispersed chiral mesoporous spheres of nanometer size with high specific area and good thermal stability were synthesized using the chiral anionic surfactant (N-palmitoyl-L-phenylalanine) as a template according to the co-structure directing agent (CSDA) method. The resulting mesoporous nanospheres were characterized using scanning electron microscopy (SEM), transmission electron microscopy (TEM), small angle X-ray powder diffraction (XRD) and nitrogen sorption experiments. The particle distribution was 190–210 nm with pore diameters of 3–4 nm. The enantioselective ability of this chiral mesoporous silica, after extraction of the chiral surfactant, was investigated by the selective adsorption of enantiomers and racemic solutions of alanine. The chiral selective adsorbability of this material type was shown by the asymmetric preferential adsorption of alanine as observed using circular dichroism (CD) spectroscopy and was further verified in a racemic mixture of valine. It was found that the adsorption of L-alanine was higher than that of D-alanine on as-prepared chiral mesoporous materials with a chiral selectivity factor of 3.15, which generates new possibilities for enantiomeric separation and other enantioselective applications.

  根据共结构导向剂（CSDA）法，使用手性阴离子表面活性剂（N-棕榈酰-L-苯丙氨酸）作为模板，合成了具有高比表面积和良好热稳定性的纳米级单分散手性介孔球。使用扫描电子显微镜（SEM）、透射电子显微镜（TEM）、小角X射线粉末衍射（XRD）和氮气吸附实验对所得介孔纳米球进行了表征。粒径分布为190-210 nm，孔径为3-4 nm。通过手性表面活性剂的萃取，通过选择性地吸附对映体和丙氨酸外消旋溶液，研究了这种手性介孔二氧化硅的对映选择性。使用圆二色光谱（CD）观察到的丙氨酸的不对称优先吸附表明了该材料类型的手性选择性吸附性，并在缬氨酸外消旋混合物中得到了进一步验证。结果发现，在制备好的手性介孔材料上，L-丙氨酸的吸附量高于D-丙氨酸，手性选择性因子为3.15，这为对映体分离和其他手性选择性应用提供了新的可能性。
• Ohkubo, Katsutoshi; Urabe, Kenji; Yamamoto, Junji, Journal of the Chemical Society. Perkin transactions I, 1995, # 23, p. 2957 - 2960
  作者：Ohkubo, Katsutoshi、Urabe, Kenji、Yamamoto, Junji、Sagawa, Takashi、Usui, Satoshi

  DOI：——

  日期：——
• Gold Nanorod@Chiral Mesoporous Silica Core–shell Nanoparticles with Unique Optical Properties
  作者：Wenjing Liu、Zhening Zhu、Ke Deng、Zhengtao Li、Yunlong Zhou、Huibin Qiu、Yan Gao、Shunai Che、Zhiyong Tang

  DOI：10.1021/ja312327m

  日期：2013.7.3

  The design and fabrication of chiral nanostructures is a promising approach to realize enantiomeric recognition and separation. In our work, gold nanorod@chiral mesoporous silica core-shell nanoparticles (GNR@CMS NPs) have been successfully synthesized. This novel material exhibits strong and tunable circular dichroism signals in the visible and near-infrared regions due to the optical coupling between the CMS shells and the GNR cores. When chiral cysteine molecules are loaded in the porous shells, the corresponding surface enhanced Raman scattering spectroscopy demonstrates a distinct chiral recognition effect, which can be used to semiquantitatively measure the composition of chiral enantiomers. A detailed sensing mechanism has been disclosed by density functional theory calculations.