di(hexadecyl) L-glutamate | 59274-90-7

• 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: di(hexadecyl) L-glutamate
• 英文别名: L-Glutamic acid, dihexadecyl ester；dihexadecyl (2S)-2-aminopentanedioate
• CAS: 59274-90-7
• 化学式: C₃₇H₇₃NO₄
• 分子量: 595.991
• InChiKey: GFLUXDVSARFPMX-DHUJRADRSA-N

物化性质

• 沸点：
  635.8±40.0 °C(Predicted)
• 密度：
  0.916±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  42
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  di(hexadecyl) L-glutamate 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 54.0h， 生成 1',3'-dixedecyl N-<1-(N-glycyl-O-benzyl ester)succinyl>-L-glutamate
  参考文献：
  名称：

  Synthetic lipidation of peptides and amino acids: monolayer structure and properties.

  摘要：

  Novel dialkyl chain amphiphiles containing peptides derived from extracellular matrix collagen ligand sequences have been synthesized using a highly efficient solid-phase approach. These compounds have been shown to form stable monolayers at the air-water interface. Monolayer features are determined by the peptide head group and are dependent on the peptide sequence. The peptide packing implied by the head group area is denser than the packing of a fully hydrated random coil structure. At high surface pressures, peptide amphiphiles can be compressed to molecular areas corresponding to fully extended peptide chains. The interfacial monolayer behavior of the peptide amphiphiles is compared to that of a series of novel compounds containing various amino acids in their head group region. Monolayers of these compounds permit investigation of model membranes containing the functional elements of proteins such as those involved in cell adhesion and signaling.

  DOI：

  10.1021/ja00142a019
• 作为产物：
  描述：

  L-谷氨酸 、 1-十六烷醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以81%的产率得到di(hexadecyl) L-glutamate
  参考文献：
  名称：

  浇铸多层薄膜中交联丙烯酸酯聚合物二维网络的模板合成

  摘要：

  浇铸多层薄膜由双链铵两亲物和双丙烯酸酯单体的水分散体制备。X 射线衍射和电子密度匹配的结构模拟表明，添加单体后，单组分 cas 膜中的层状分子堆积发生了变化，从而使单体可以均匀地结合到双层表面附近的空隙中。X射线光电子能谱测定的元素分布深度剖面与这一假设一致

  DOI：

  10.1021/ja00005a044

文献信息

• Reagent for introduction of protein or gene
  申请人：Waseda University

  公开号：US08338643B2

  公开（公告）日：2012-12-25

  The present invention provides a reagent for introducing a protein or gene into a cell. The reagent of the present invention is, for example, a reagent for introducing a protein or gene into a cell, which comprises a composition comprising a cationic amino acid type lipid represented by the following formula (I)-1: (wherein in formula (I)-1: L is a single bond, —CONH—, or —S—S—; M1 is —(CH2)k— or —(CH2CH2O)k— (wherein k is an integer between 0 and 14); and m1 and m2 are each independently an integer between 11 and 21 (in this regard, when providing a reagent for introducing a gene into a cell, the case where both m1 and m2 are 15 is excluded)).

  本发明提供了一种用于将蛋白质或基因引入细胞的试剂。本发明的试剂例如是一种用于将蛋白质或基因引入细胞的试剂，包括以下式(I)-1所代表的阳离子氨基酸型脂质的组合物： （其中在式(I)-1中：L是单键，—CONH—，或—S—S—；M1是—(CH2)k—或—(CH2CH2O)k—（其中k是0到14之间的整数）；m1和m2分别是介于11和21之间的整数（在这方面，当提供一种用于将基因引入细胞的试剂时，排除了m1和m2都为15的情况）。
• Synthesis and evaluation of novel lipopeptide as a vehicle for efficient gene delivery and gene silencing
  作者：O.O. Koloskova、A.A. Nikonova、U.A. Budanova、I.P. Shilovskiy、I.A. Kofiadi、A.V. Ivanov、O.A. Smirnova、V.V. Zverev、Yu.L. Sebaykin、S.M. Andreev、M.R. Khaitov

  DOI：10.1016/j.ejpb.2016.03.014

  日期：2016.5

  promising amphiphile for liposomal formation OrnOrnGlu(C16H33)2 was examined more carefully. It has been shown that the lipopeptide possesses low toxicity (in vitro and in vivo) and high transfection efficiency with pDNA and siRNA in different cell lines. In addition, the production of liposomes based on this lipopeptide is simple, quick and cheap. Thus OrnOrnGlu(C16H33)2 is a promising vehicle for gene delivery

  基于核酸的疗法最近已成为新一代的新一代药物，用于治疗和预防病毒感染，癌症和遗传疾病，但由于其向靶细胞的递送相对较弱，因此其广泛使用受到限制。具有肽亲水结构域的合成阳离子两亲物用作非病毒基因递送的试剂是一种有吸引力的方法。我们开发了合成脂族肽的方案，该脂族肽在疏水域中具有不同的烃链长度，而在极性头中具有不同的氨基酸。对于获得的衍生物，我们确定了转染效率，临界囊泡浓度，粒径，ζ电位和聚集体稳定性。我们发现，如果鸟氨酸是两亲物中极性头的一部分，则转染效率会提高。脂质体形成OrnOrnGlu（C 16 H 33）2最有希望的两亲物被更仔细地检查。已经显示脂肽在不同细胞系中具有低毒性（体外和体内）和高pDNA和siRNA的转染效率。另外，基于该脂肽的脂质体的生产是简单，快速和廉价的。因此，OrnOrnGlu（C 16 H 33）2是用于基因传递和基因沉默的有前途的载体。
• CARBOXYLIC ACID-TYPE LIPID, AND LIPID PARTICLE AND LIPID MEMBRANE EACH COMPRISING CARBOXYLIC ACID-TYPE LIPID
  申请人：Toray Industries, Inc.

  公开号：US20210387943A1

  公开（公告）日：2021-12-16

  A carboxylic acid-type lipid can accelerate adhesion or aggregation of platelets even if the carboxylic acid-type lipid does not carry a protein involved in adhesion or aggregation of platelets or a peptide corresponding to an active site of the protein; a lipid particle and a lipid membrane each include the carboxylic acid-type lipid; and a platelet aggregation accelerating agent, a platelet adhesion accelerating agent, a hemostatic agent and a platelet substitute each include the carboxylic acid-type lipid, the lipid particle or the lipid membrane. A carboxylic acid-type lipid is selected from carboxylic acid-type lipids represented by formulas (I) to (VI), a lipid particle includes the carboxylic acid-type lipid, a lipid membrane includes the carboxylic acid-type lipid, and a platelet aggregation accelerating agent, a platelet adhesion accelerating agent, a hemostatic agent and a platelet substitute each include the carboxylic acid-type lipid, the lipid particle or the lipid membrane.

  一种羧酸型脂质即使不携带与血小板粘附或聚集有关的蛋白质或相应的蛋白质活性位点对血小板的粘附或聚集也能加速，脂质颗粒和脂质膜均包括该羧酸型脂质；血小板聚集加速剂、血小板粘附加速剂、止血剂和血小板替代物均包括该羧酸型脂质、脂质颗粒或脂质膜。所述羧酸型脂质选自公式（I）到（VI）所表示的羧酸型脂质，脂质颗粒包括该羧酸型脂质，脂质膜包括该羧酸型脂质，血小板聚集加速剂、血小板粘附加速剂、止血剂和血小板替代物均包括该羧酸型脂质、脂质颗粒或脂质膜。
• Synthesis of model glycolipids having two long alkyl chains
  作者：Zhongzhi Zhang、Kimitoshi Fukunaga、Toshimi Shimizu、Katsumi Nakao

  DOI：10.1016/0008-6215(95)00298-8

  日期：1995.11
• pH-sensitive cationic lipopeptides for the design of drug-delivery systems
  作者：Yu. L. Sebyakin、U. A. Budanova

  DOI：10.1134/s1068162006050025

  日期：2006.9

  Lipopeptides on the basis of L-glutamic acid and glutamine di- and monoesters with aliphatic alcohols of various lengths that contain L-arginine, L-ornithine, and L-lysine were synthesized. The behavior of these amphiphiles in aqueous medium was shown to depend on their structure.