tetradecanoate | 1715-79-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tetradecanoate
• 英文别名: tetradecanoate ion；myristate anion；myristate；sodium myristate
• CAS: 1715-79-3
• 化学式: C₁₄H₂₇O₂
• 分子量: 227.367
• InChiKey: TUNFSRHWOTWDNC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetradecanoate 、 对甲苯磺酰氯 生成 (4-methylphenyl)sulfonyl tetradecanoate
  参考文献：
  名称：

  Al-Lohedan, Hamad A., Journal of Chemical Research, Miniprint, 1991, # 8, p. 2066 - 2090

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯肉豆蔻酸酯 在 N-hexadecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide 作用下， 以 水 为溶剂， 生成 tetradecanoate 、 4-硝基苯酚阴离子
  参考文献：
  名称：

  Micellization and Catalytic Properties of Cationic Surfactants with Head Groups Functionalized with a Hydroxyalkyl Fragment

  摘要：

  The catalytic activity of two homological series of cationic surfactants bearing a hydroxyalkyl fragment in the head groups R(CH3)(2)N+(CH2CH2OH)Br- and R(CH3)(2)N+(CH2CH2CH2OH)Br- toward the cleavage of the p-nitrophenyl esters of carbonic acids of different hydrophobicity (acetate, caprilate, caprinate, laurate, myristate) is shown to exceed that of typical cationic surfactants with the trimethylammonium (TMA) headgroup. The catalytic effect increases with the alkyl chain length of surfactants and nonmonotonous changes in the series: acetate < caprilate < myristate < laurate < caprinate, reaching 750 times. NMR and IR spectroscopy studies and the surface potential calculations revealed that the higher catalytic effect of hydroxyalkylated surfactants is not due to their higher surface potential and binding capacity toward substrates. This is in line with finding that binding constants for TMA series are higher than for their hydroxyalkylated analogues, which was demonstrated by the fitting of kinetic data in terms of the pseudophase model. The microenvironment factor rather than concentrating effect is responsible for the advanced catalytic properties of hydroxyalkylated surfactants in the micellar phase.

  DOI：

  10.1021/je300753d
• 作为试剂：
  描述：

  邻硝基苯甲醇 、 三乙胺 、 十八烷酰氯 、 在 三乙胺盐酸盐 、 乙醇 、 tetradecanoate 、 十六烷酸酯 、 Margarate 、 Octadec-9-enoate 、 esters 、 邻硝基苯甲醇 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 2-Nitrobenzyl octadecanoate
  参考文献：
  名称：

  Photolabile blocked surfactants and compositions containing the same

  摘要：

  本发明提供了一种被光敏保护或掩蔽基团阻止表面活性剂作用（在此称为“光敏可逆阻滞表面活性剂”），但在接受活性辐射照射后变得不受阻拦的表面活性剂。通过将光敏可逆阻滞表面活性剂与聚合膜形成材料混合，可以提供在辐射下形成表面活性剂的涂层组合物。含有光敏可逆阻滞表面活性剂的组合物在用作各种基材的保护涂层或压敏胶带中的粘合剂时非常有用。虽然最初与基材粘合良好，但在经过适当的辐射照射后，这些组合物可以轻松地从基材上移除，因为表面活性剂已被解除阻滞，恢复了其表面活性。

  公开号：

  US04478967A1

文献信息

• Characterization of LipN (Rv2970c) of<i>Mycobacterium Tuberculosis</i>H37Rv and its Probable Role in Xenobiotic Degradation
  作者：Dipendrasinh Jadeja、Nandita Dogra、Stuti Arya、Gurpreet Singh、Gurdyal Singh、Jagdeep Kaur

  DOI：10.1002/jcb.25285

  日期：2016.2

  RHC-80267 and N-bromosuccinimide inhibited LipN enzyme activity completely. Interestingly, Trp145, a non active-site residue, demonstrated functional role to retain enzyme activity. The enzyme was localized in cytosolic fraction of M. tuberculosis H37Rv. The enzyme was able to synthesize ester of butyric acid, methyl butyrate, in presence of methanol. LipN was able to hydrolyze 4-hydroxyphenylacetate

  LipN（Rv2970c）属于结核分枝杆菌H37Rv的Lip家族，与人激素敏感性脂肪酶同源。该酶表现出对短碳链底物的偏爱，该底物在45℃/ pH 8.0下具有最佳活性，在pH 6.0至9.0之间具有稳定性。该酶的比活为217 U / mg蛋白，pNP丁酸酯为底物。将三丁酸甘油酯水解为二丁酸和一丁酸。确认该酶的活性位点残基为Ser216，Asp316和His346。Tetrahydrolipstatin，RHC-80267和N-溴代琥珀酰亚胺可完全抑制LipN酶的活性。有趣的是，非活性位点残基Trp145表现出保留酶活性的功能。该酶位于结核分枝杆菌H37Rv的胞质级分中。该酶能够合成丁酸的酯，丁酸甲酯，在甲醇存在下。LipN能够将4-羟基苯乙酸酯水解为对苯二酚。该基因在体外生长条件下不表达，而在结核分枝杆菌H37Ra巨噬细胞感染后6小时观察到了rv2970c基因的表达。在个别体外应激条件下，
• A Single Active-Site Mutation of P450BM-3 Dramatically Enhances Substrate Binding and Rate of Product Formation
  作者：Donovan C. Haines、Amita Hegde、Baozhi Chen、Weiqiang Zhao、Muralidhar Bondlela、John M. Humphreys、David A. Mullin、Diana R. Tomchick、Mischa Machius、Julian A. Peterson

  DOI：10.1021/bi201099j

  日期：2011.10.4

  Identifying key structural features of cytochromes P450 is critical in understanding the catalytic mechanism of these important drug-metabolizing enzymes. Cytochrome P450BM-3 (BM-3), a structural and mechanistic P450 model, catalyzes the regio- and stereoselective hydroxylation of fatty acids. Recent work has demonstrated the importance of water in the mechanism of BM-3, and site-specific mutagenesis

  识别细胞色素 P450 的关键结构特征对于理解这些重要的药物代谢酶的催化机制至关重要。细胞色素 P450BM-3 (BM-3) 是一种结构和机械 P450 模型，可催化脂肪酸的区域和立体选择性羟基化。最近的工作证明了水在 BM-3 机制中的重要性，而定点诱变有助于阐明底物识别、结合和产物形成的机制。确定在 BM-3 活性位点中起关键作用的氨基酸之一是丙氨酸 328，它位于 K 螺旋和 β 1-4 之间的环中。在 A328V BM-3 突变体中，与野生型酶相比，底物亲和力增加了 5-10 倍，周转数增加了 2-8 倍。与野生型酶不同，这种突变体是从由于较高的结合亲和力，大肠杆菌与内源性底物结合。对底物结合的天然 BMP 和 A328V 突变 BMP 的晶体结构的仔细检查表明，底物的定位在两种形式的酶中基本相同，两个缬氨酸甲基占据野生活性位点中存在的空隙型底物结合结构。
• Method for protein N-myristoylation
  申请人：Washington University

  公开号：US05504008A1

  公开（公告）日：1996-04-02

  There is disclosed a method for providing for the coexpression of N-myristoyltransferase and a protein substrate for said N-myristoyltransferase in E. coli comprising introducing into E. coli a dual plasmid system comprising (A) the isopropyl-.beta.-D-thiogalactopyranoside-inducible tac promoter, the g10-L ribosome binding site, a NMT gene, the kanamycin resistance gene and the p15A origin of replication in operable sequence and (B) the recA promoter, the g10-L ribosome binding site, a mammalian gene, the ampicillin resistance gene and the Col E1 origin of replication in operable sequence. This allows production of mammalian N-myristoylproteins or proteins containing covalently linked analogs of myristate with altered physical-chemical properties.

  本发明揭示了一种在大肠杆菌中提供N-肉豆蔻酰转移酶和蛋白底物共表达的方法，包括引入双质粒系统到大肠杆菌中，该系统包括（A）丙酮酸异丙酯-β-D-硫代半乳糖苷诱导的tac启动子，g10-L核糖体结合位点，NMT基因，卡那霉素耐药基因和p15A复制起点可操作序列，以及（B）recA启动子，g10-L核糖体结合位点，哺乳动物基因，氨苄青霉素耐药基因和Col E1复制起点可操作序列。这允许生产哺乳动物N-肉豆蔻酰蛋白或含有改变物理化学性质的共价连接的肉豆蔻酸类似物的蛋白。
• Antipsychotic drug
  申请人：Nippon Oil & Fats Co., Ltd.

  公开号：US05112863A1

  公开（公告）日：1992-05-12

  The present invention provides an antipsychotic drug containing essentially an N-acyl amino acid derivative represented by the following general formula: RCO-A wherein R indicates an alkyl or alkenyl having 1-25 carbon atoms, and A is an amino acid residue. The compound is similar to natural products and has little side effect by acting directly to brain cells after passing through easily the blood brain barrier.

  本发明提供了一种抗精神病药物，其基本上包含以下通式所代表的N-酰基氨基酸衍生物：RCO-A，其中R表示具有1-25个碳原子的烷基或烯基，A是氨基酸残基。该化合物类似于天然产物，并且通过易于通过血脑屏障直接作用于脑细胞，具有很少的副作用。
• Linker-Based Lecithin Microemulsion Delivery Vehicles
  申请人：Acosta-Zara Edgar Joel

  公开号：US20080139392A1

  公开（公告）日：2008-06-12

  The present invention relates to biocompatible microemulsion systems designed for controlled release drug delivery applications formulated with phospholipids such as lecithin (surfactant), a lipophilic additive (linker) containing 9 or more carbons in their alkyl group and hydrophilic-lipophilic balance (HLB) of 5 or less, and a surfactant-like hydrophilic additive (linker) containing between 6 to 9 carbon atoms in their alkyl tail. The combination of linkers and phospholipids produce formulations capable of delivering high concentrations of poorly soluble drugs into epithelial tissue using low surfactant concentrations, with minimum cytotoxic side effects.

  本发明涉及生物相容性微乳液系统，用于控制释放药物的应用，其配方包括磷脂类物质，如卵磷脂（表面活性剂），含有9个或更多碳原子的疏水性添加剂（连接剂），以及亲水-疏水平衡（HLB）为5或更低的类表面活性剂的亲水性添加剂（连接剂），连接剂和磷脂类物质的组合可产生配方，能够使用低表面活性剂浓度将高浓度的难溶性药物输送到上皮组织中，且具有最小的细胞毒性副作用。