N-十六碳酰基-L-丙氨酸 | 56255-31-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 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-十六碳酰基-L-丙氨酸
• 中文别名: N-十六酰基-L-丙氨酸
• 英文名称: N-palmitoyl-L-alanine
• 英文别名: N-palmitoyl alanine；N-n-hexadecanoyl (L)-alanine；palmitoyl-L-alanine；Palmitoyl alanine；(2S)-2-(hexadecanoylamino)propanoic acid
• CAS: 56255-31-3
• 化学式: C₁₉H₃₇NO₃
• 分子量: 327.508
• InChiKey: NRBFOSKZAWRBJI-KRWDZBQOSA-N

物化性质

• LogP：
  6.370 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-十六碳酰基-L-丙氨酸 在 水 、 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 palmitoyl-L-alanyl-L-phenylalanine
  参考文献：
  名称：

  The striking influence of SWNT–COOH on self-assembled gelation

  摘要：

  极少量的 f-SWNT 通过触发超分子凝胶中互连自组装纤维网络 (SAFIN) 的形成，显着提高（±17 倍）两亲分子的凝胶效率。

  DOI：

  10.1039/c2cc16567h
• 作为产物：
  描述：

  棕榈酰氯 在 sodium hydroxide 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 7.0h， 生成 N-十六碳酰基-L-丙氨酸
  参考文献：
  名称：

  Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids

  摘要：

  A variety of fatty acid amides of different naturally occurring L-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them L-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.028

文献信息

• Elucidating the Structural Requirement of Uridylpeptide Antibiotics for Antibacterial Activity
  作者：Yuma Terasawa、Chisato Sataka、Toyotaka Sato、Kazuki Yamamoto、Yukari Fukushima、Chie Nakajima、Yasuhiko Suzuki、Akira Katsuyama、Takanori Matsumaru、Fumika Yakushiji、Shin-ichi Yokota、Satoshi Ichikawa

  DOI：10.1021/acs.jmedchem.0c00973

  日期：2020.9.10

  The synthesis and biological evaluation of analogues of uridylpeptide antibiotics were described, and the molecular interaction between the 3′-hydroxy analogue of mureidomycin A (3′-hydroxymureidomycin A) and its target enzyme, phospho-MurNAc-pentapeptide transferase (MraY), was analyzed in detail. The structure–activity relationship (SAR) involving MraY inhibition suggests that the side chain at the

  描述了尿苷肽抗生素类似物的合成和生物学评估，并证明了莫来霉素A（3'-羟基尿素霉素A）的3'-羟基类似物与其靶酶磷酸-MurNAc-五肽转移酶（MraY）之间的分子相互作用。详细分析。涉及MraY抑制的结构活性关系（SAR）表明，尿素-二肽部分的侧链不影响MraY抑制。但是，抗铜绿假单胞菌活性形成了鲜明的对比，而尿素-二肽基序是关键的贡献者。还建议核苷肽渗透酶NppA1A2BCD负责3'-羟基mureidomycin A进入细胞质的转运。进一步进行了3'-羟基mureidomycin A尿素-二肽部分的系统SAR分析，并确定了抗菌活性。该研究为基于尿苷肽抗生素的类似物的合理设计提供了指导。
• Superior SWNT dispersion by amino acid based amphiphiles: designing biocompatible cationic nanohybrids
  作者：Sayanti Brahmachari、Dibyendu Das、Prasanta Kumar Das

  DOI：10.1039/c0cc02464c

  日期：——

  Stable aqueous SWNT dispersion up to 92% was achieved using amino acid based amphiphiles through a structure–property investigation. The nanohybrids showed remarkable serum stability and biocompatibility to mammalian cells.

  通过结构–性能研究，利用氨基酸基表面活性剂实现了高达92%稳定性的水溶性SWNT分散。这些纳米复合物表现出卓越的血液稳定性及对哺乳动物细胞的生物相容性。
• Ionic Liquid Crystals Derived from Amino Acids
  作者：Markus Mansueto、Wolfgang Frey、Sabine Laschat

  DOI：10.1002/chem.201302319

  日期：2013.11.18

  Novel chiral amino acid derived ionic liquid crystals with amine and amide moieties as spacers between the imidazolium head group and the alkyl chain were synthesised. The key step in the synthesis utilised the relatively uncommon SO3 leaving group in a microwave‐assisted reaction. The mesomorphic properties of the mesogens were determined by differential scanning calorimetry (DSC), polarising optical

  合成了新型的手性氨基酸衍生的离子型液晶，其胺和酰胺部分作为咪唑鎓头基和烷基链之间的间隔基。合成中的关键步骤利用了相对罕见的SO 3微波辅助反应中的离去基团。介晶的介晶性质是通过差示扫描量热法（DSC），偏振光学显微镜（POM）和X射线衍射确定的。所有液晶盐均表现出具有强相互指状的双层结构的近晶A中间相几何形状。立体生成中心的空间体积的增加阻碍了中间相的形成。在苯丙氨酸衍生的衍生物的情况下，与其他氨基酸衍生物相比，烷基链较短的同构行为被观察到，表明苯基部分具有额外的稳定作用。
• [EN] HUMAN MICROBIOTA DERIVED N-ACYL AMIDES FOR THE TREATMENT OF HUMAN DISEASE<br/>[FR] N-ACYL AMIDES DÉRIVÉS DU MICROBIOTE HUMAIN POUR LE TRAITEMENT D'UNE MALADIE HUMAINE
  申请人：UNIV ROCKEFELLER

  公开号：WO2019006246A1

  公开（公告）日：2019-01-03

  The present invention provides compositions and methods for the modulation of G protein-coupled receptors (GPCRs). The invention provides a genetically engineered cell, wherein the cell expresses a human microbial N-acyl synthase (hm-NAS) gene. In one embodiment, the hm-NAS gene is N-acyl serinol synthase. The invention provides a probiotic composition, the probiotic composition comprises a genetically engineered cell of the invention. The invention provides a method for modulating a G protein-coupled receptor (GPCR) activity in a subject, the method comprises administering to the subject an effective amount of a composition comprising at least one selected from the group consisting of a genetically engineered cell, an hm-NAS gene, and a N-acyl amide.

  本发明提供了用于调节G蛋白偶联受体（GPCRs）的组合物和方法。该发明提供了一种基因工程细胞，其中该细胞表达人类微生物N-酰基合酶（hm-NAS）基因。在一个实施例中，hm-NAS基因是N-酰丝氨醇合酶。该发明提供了一种益生菌组合物，该益生菌组合物包括该发明的基因工程细胞。该发明提供了一种调节受体内G蛋白偶联受体（GPCR）活性的方法，该方法包括向受体施用包含至少选自基因工程细胞、hm-NAS基因和N-酰胺的组合物的有效量。
• Organic compounds
  申请人：Givaudan S.A.

  公开号：US10836712B2

  公开（公告）日：2020-11-17

  A flavour composition comprising a compound according to the formula (I) or edible salts thereof, wherein R1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR2R3, in which R3 is H or together with R2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

  一种包含符合式(I)的化合物或其可食用盐的风味组合物，其中R1是含有6至20个碳原子的烷基残基，或者含有9至25个碳原子且具有1至6个双键的烯烃残基，R1与其连接的羰基一起是羧酸的残基，NR2R3中，R3为H或与R2和它们连接的N原子一起是一个5元环的残基，是一种氨基酸的残基，特别是一种蛋白质原性氨基酸、鸟氨酸、γ-氨基丁酸或β-丙氨酸，或者是一种1-氨基环烷基羧酸的残基。