N-dodecanoyl-L-tyrosine | 34158-61-7

• 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: N-dodecanoyl-L-tyrosine
• 英文别名: CSL12-E；N-(1-oxododecanyl)-L-tyrosine；N-Lauroyltyrosin；N-lauroyl-L-tyrosine；(S)-2-dodecanamido-3-(4-hydroxyphenyl )propanoic acid；(2S)-2-(dodecanoylamino)-3-(4-hydroxyphenyl)propanoic acid
• CAS: 34158-61-7
• 化学式: C₂₁H₃₃NO₄
• 分子量: 363.497
• InChiKey: SVQAZCRYIXURJT-IBGZPJMESA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  586.4±45.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-methyl 2-(dodecanamido)-3-(4-hydroxyphenyl)propanoate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以91%的产率得到N-dodecanoyl-L-tyrosine
  参考文献：
  名称：

  Multi-stimuli responsive self-healing metallo-hydrogels: tuning of the gel recovery property

  摘要：

  基于一系列含酪氨酸的两性分子发现了可自修复、多刺激响应的金属水凝胶。这些金属凝胶的形成对Ni²⁺离子高度选择性。此外，自愈合性能可以通过改变相应凝胶体两性分子的链长来调节。

  DOI：

  10.1039/c3cc48896a

文献信息

• Synthetic libraries of tyrosine-derived bacterial metabolites
  作者：Savvas N. Georgiades、Jon Clardy

  DOI：10.1016/j.bmcl.2007.10.058

  日期：2008.5

  The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters

  据报道，制备了 131 个小分子的集合，让人联想到长链 N-酰基酪氨酸、烯酰胺和烯醇酯家族，这些分子是从大肠杆菌环境 DNA (eDNA) 的异源表达中分离出来的。N-酰基酪氨酸及其3-酮对应物的合成库是通过固相途径制备的，而烯酰胺和烯醇酯是在溶液相中合成的。
• Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus
  作者：Chee Wee Phoon、Brinda Somanadhan、Sabrina Cher Hui Heng、Anna Ngo、Siew Bee Ng、Mark S. Butler、Antony D. Buss、Mui Mui Sim

  DOI：10.1016/j.tet.2004.09.046

  日期：2004.12

  as a minor component. Gymnastatin N (1) was found to be a 52:48 mixture of (1S,6′R) and (1R,6′R) diastereomers, by synthesis of the four possible diastereomers and comparison of the optical rotation and chiral HPLC profile of each diastereoisomer with the natural product. Analogues of 1 were synthesized and evaluated against the Plk1 assay and these SAR studies suggested that the diene and free carboxylic

  针对POLO样激酶1（Plk1）（一种抗癌靶标）的高通量筛选，鉴定了一种来自点状真菌Arachniotus punctatus的活性提取物。生物测定指导的分馏导致分离出新的天然产物gymaststatin N（1）和已知的化合物阿诺洛糖醇A（2），IC 50值分别为13和118μM 。分离出金格他汀N，3的12'-羟基类似物作为次要成分。Gymnastatin N（1）被认为是（1的52:48混合物小号，6' - [R ）和（1 - [R，6' - [R）非对映异构体，可以合成四种可能的非对映异构体，并比较每种非对映异构体与天然产物的旋光度和手性HPLC谱。合成了类似物1并针对Plk1分析进行了评估，这些SAR研究表明，二烯和游离羧酸部分可能是其生物活性的原因。
• Synthesis of Lipoamino Acids and Their Activity against Cerebral Ischemic Injury
  作者：Li-Yun Yao、Qi Lin、Yin-Yao Niu、Ke-Min Deng、Jian-Hua Zhang、Yang Lu

  DOI：10.3390/molecules14104051

  日期：——

  A series of lipoamino acids were synthesized and their neuroprotective effect against brain ischemia induced by oxygen-glucose deprivation (OGD) on rat cerebral slices was evaluated. Among these compounds, N-stearoyl-L-tyrosine (4), N-stearoyl-L-serine (5) and N-stearoyl-L-threonine (6) exhibited good neuroprotective activity. We found that the neuroprotective activity of lipoamino acids depended on the acyl group, the presence of a free carboxylic function and a free hydroxyl group at the branched chain of the amino acids. The results also showed that 5 was the most active compound, protecting rat brain slices against OGD as well as hydrogen peroxide (H2O2) insult at the range of 1–10 M.

  一系列脂氨基酸被合成，并评估了它们对大鼠脑片由氧葡萄糖剥夺（OGD）诱导的脑缺血的神经保护作用。在这些化合物中，N-硬脂酰基-L-酪氨酸（4）、N-硬脂酰基-L-丝氨酸（5）和N-硬脂酰基-L-苏氨酸（6）表现出了良好的神经保护活性。我们发现，脂氨基酸的神经保护活性依赖于酰基团、氨基酸支链上自由羧基和自由羟基的存在。结果还显示，5是最活跃的化合物，在1-10 M的范围内保护大鼠脑片免受OGD和过氧化氢（H2O2）的损伤。
• The Catalytic Action of a Mixed Micelle of Lauroylamino Acid and a Detergent
  作者：Tohru Inoue、Kazuo Nomura、Hideo Kimizuka

  DOI：10.1246/bcsj.49.719

  日期：1976.3

  of the mixed micelles of lauroylamino acids (LauAm) and detergents on the hydrolysis of p-nitrophenyl acetate has been studied. The amino acids used for the synthesis of LauAm were glycine, serine, histidine, tyrosine, lysine, and arginine. Cetyltrimethylammonium bromide (CTAB), polyoxyethylene dodecyl ether (C12E6) and sodium dodecyl sulfate (SDS) were used for the preparation of the mixed micelles

  研究了月桂酰氨基酸 (LauAm) 和洗涤剂的混合胶束对乙酸对硝基苯酯水解的催化作用。用于合成 LauAm 的氨基酸是甘氨酸、丝氨酸、组氨酸、酪氨酸、赖氨酸和精氨酸。使用十六烷基三甲基溴化铵（CTAB）、聚氧乙烯十二烷基醚（C12E6）和十二烷基硫酸钠（SDS）制备含有LauAm的混合胶束。在使用的洗涤剂中，只有 CTAB 显着增强了 LauAm 的催化活性。提出了反应方案，并从动力学数据估计了 LauAm 催化活性的速率常数。还研究了pH的影响。在本研究的基础上讨论了催化作用的机理。
• Pharmaceutical formulations for the oral delivery of peptide or protein drugs
  申请人：Cyprumed GmbH

  公开号：EP3006045A1

  公开（公告）日：2016-04-13

  The present invention relates to improved pharmaceutical formulations, uses and methods for the oral delivery of peptide or protein drugs with advantageously high bioavailability, safety and cost-effectiveness. In particular, the invention provides a peptide or protein drug having a molecular weight of equal to or less than about 50 kDa for use as a medicament, wherein said peptide or protein drug is to be administered orally in combination with a pharmaceutically acceptable copper salt/complex and/or a pharmaceutically acceptable zinc salt/complex, and with a pharmaceutically acceptable reducing agent. The invention also provides a pharmaceutical composition comprising: a peptide or protein drug having a molecular weight of equal to or less than about 50 kDa; a pharmaceutically acceptable copper salt/complex and/or a pharmaceutically acceptable zinc salt/complex; and a pharmaceutically acceptable reducing agent.

  本发明涉及肽或蛋白质药物口服给药的改进药物制剂、用途和方法，具有生物利用度高、安全性好和成本效益高等优点。特别是，本发明提供了一种分子量等于或小于约 50 kDa 的多肽或蛋白质药物，可用作药物，其中所述多肽或蛋白质药物将与药学上可接受的铜盐/络合物和/或药学上可接受的锌盐/络合物以及药学上可接受的还原剂一起口服给药。本发明还提供了一种药物组合物，其中包括：分子量等于或小于约 50 kDa 的多肽或蛋白药物；药学上可接受的铜盐/络合物和/或药学上可接受的锌盐/络合物；以及药学上可接受的还原剂。