N-tetradecanoyl-L-tyrosine

• 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-tetradecanoyl-L-tyrosine
• 英文别名: n-Myristoyltyrosine；(2S)-3-(4-hydroxyphenyl)-2-(tetradecanoylamino)propanoic acid
• 化学式: C₂₃H₃₇NO₄
• 分子量: 391.551
• InChiKey: JWVQCQGVVNUXFW-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  阿糖胞苷 、 N-tetradecanoyl-L-tyrosine 在 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 N-((S)-1-((1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)tetradecanamide
  参考文献：
  名称：

  Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine

  摘要：

  1-beta-D-Arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlympbocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N-4 derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S-180 tumor while others showed a decreased activity in comparison with Ara-C. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.028
• 作为产物：
  描述：

  L-酪氨酸甲酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 28.33h， 生成 N-tetradecanoyl-L-tyrosine
  参考文献：
  名称：

  糖和脂肪酸对N-脂肪酰基-L-酪氨酸糖苷配基生物活性的影响

  摘要：

  摘要在本研究中，一系列的脂肪酸为基础的（短期，中期和长期的不饱和链）糖基化的ñ -脂肪酸酰基大号-tyrosines和Ñ -lipoyl-大号-酪氨酸甲酯的合成和评价了它们的细胞毒性和抗菌活性。使用不同的化学试剂合成糖苷配基部分。使用路易斯酸\（\ hbox {BF} _ {3。} \ hbox {Et} _ {2} \ hbox {O} \）对糖苷配基部分与不同的碳水化合物进行糖基化。针对一组四个癌细胞系测试了所有合成的化合物。糖基化的N-脂肪酰基-L-酪氨酸对所有细胞系均具有中等活性\（\ hbox {IC} _ {50} \）值在\（15.6 {-} 45.6 \; {\ upmu} \ hbox {M} \）范围内。但是，油酸类似物（10a，10d）对MDA的\（\ hbox {IC} _ {50} \）值分别为15.6，\（17.6 \; {\ upmu} \ hbox {M} \）

  DOI：

  10.1007/s12039-017-1298-y

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。
• Multi-stimuli responsive self-healing metallo-hydrogels: tuning of the gel recovery property
  作者：Shibaji Basak、Jayanta Nanda、Arindam Banerjee

  DOI：10.1039/c3cc48896a

  日期：——

  Self-healable, multi-stimuli responsive metallo-hydrogels based on a series of tyrosine containing amphiphiles have been discovered. Formation of these metallo-gels is highly selective to Ni²⁺ ions. Moreover, the self-healing property can be modulated by varying the chain length of the corresponding gelator amphiphiles.

  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。
• [EN] FATTY ACID ACYLATED D-AMINO ACIDS FOR ORAL PEPTIDE DELIVERY<br/>[FR] ACIDES D-AMINÉS ACYLÉS PAR UN ACIDE GRAS POUR L'ADMINISTRATION DE PEPTIDES PAR VOIE ORALE
  申请人：NOVO NORDISK AS

  公开号：WO2014060447A1

  公开（公告）日：2014-04-24

  The present invention relates to fatty acid acylated amino acids (FA-Daa's) acting as permeation enhancers for oral delivery of therapeutic macromolecules such as peptides and pharmaceutical compositions comprising such FA-Daa's.

  本发明涉及脂肪酸酰化氨基酸（FA-Daa's）作为渗透增强剂，用于口服输送治疗性大分子，如肽和包含这种FA-Daa's的药物组合物。
• Fatty Acid Acylated D-Amino Acids for Oral Peptide Delivery
  申请人：Novo Nordisk A/S

  公开号：US20150265710A1

  公开（公告）日：2015-09-24

  The present invention relates to fatty acid acylated amino acids (FA-Daa's) acting as permeation enhancers for oral delivery of therapeutic macromolecules such as peptides and pharmaceutical compositions comprising such FA-Daa's.

  本发明涉及脂肪酸酰化氨基酸（FA-Daa），其作为渗透增强剂用于口服治疗大分子药物，如肽类，并包括含有这些FA-Daa的制药组合物。
• Liposome delivery of compositions to enhance tanning and repair UV damage
  申请人：CALIFORNIA SUNCARE INC.

  公开号：EP0707844A2

  公开（公告）日：1996-04-24

  The present invention concerns the delivery in carrier liposomes of novel combinations of two or more active ingredients designed to enhance tanning and ameliorate damage to skin and DNA caused by UV radiation.

  本发明涉及在载体脂质体中输送两种或两种以上活性成分的新型组合，旨在增强美黑效果并改善紫外线辐射对皮肤和 DNA 造成的损伤。