棕榈酰谷氨酸 | 38079-66-2

• 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: 棕榈酰谷氨酸
• 英文名称: N-hexadecanoyl-L-glutamic acid
• 英文别名: N-palmitoyl-L-glutamic acid；2-palmitamidoglutaric acid；N-palmitoylglutamic acid；Palmitoyl glutamic acid；palmitoylglutamic acid；palmGlu；(2S)-2-(hexadecanoylamino)pentanedioic acid
• CAS: 38079-66-2
• 化学式: C₂₁H₃₉NO₅
• 分子量: 385.544
• InChiKey: KMAOMYOPEIRFLB-SFHVURJKSA-N

物化性质

• 沸点：
  581.1±40.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：125 mg/mL（324.22 mM；需要超声波）
• LogP：
  5.002 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  27
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 储存条件：
  -20°C

制备方法与用途

生物活性

棕榈酰谷氨酸（N-棕榈酰-L-谷氨酸）是一种酰基氨基酸，不仅具有神经保护作用，还被用作化妆品原料。

反应信息

• 作为反应物：
  描述：

  十二烷基二甲基叔胺 、 棕榈酰谷氨酸 以 乙醇 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  pH-sensitive Wormlike Micelle and Hydrogel Formation by Acylglutamic Acid–Alkylamine Complex

  摘要：

  通过形成蠕虫样胶束和水凝胶获得了pH敏感的粘弹性流体。这些聚集体是由脂肪酸谷氨酸（CnGlu）与叔烷基胺以1:1的化学计量比形成的复合物。pH敏感特性反映了CnGlu头部周围电荷密度的变化，从而控制了分子聚集体的曲率。链较长的CnGlu类似物在狭窄的pH区域内产生水凝胶。本研究提出了一种通过类双子表面活性剂获得刺激响应型粘弹性流体的独特方法。

  DOI：

  10.1246/cl.160231
• 作为产物：
  描述：

  棕榈酸 在 magnesium sulfate 、 对甲苯磺酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 xylene 为溶剂， 反应 11.0h， 生成 棕榈酰谷氨酸
  参考文献：
  名称：

  Higher N-acyl-L-amino acid derivatives

  摘要：

  A preparative method is proposed for obtaining higher N-acylamino acids by reaction of free amino acids with fatty acid nitrophenyl esters. It was shown that these acids can transport positive ions through a liquid lipophilic medium. A direct method is proposed for obtaining fatty acid 4-nitrophenyl esters by boiling 4-nitrophenol and the fatty acid in xylene in a Soxhlet apparatus in the presence of an acid catalyst.

  DOI：

  10.1007/bf00958844

文献信息

• GIP-GLP-1 DUAL AGONIST COMPOUNDS AND METHODS
  申请人：Zealand Pharma A/S/

  公开号：US20150299281A1

  公开（公告）日：2015-10-22

  The present invention relates to truncated GIP analogues which comprise one or more substitutions as compared to wild-type GIP and which may have the property of an altered, preferably increased GLP-1 activity, e.g. as assessed in in vitro efficacy assays. The invention provides GIP-GLP-1 dual agonist compounds and associated methods.

  本发明涉及截短的GIP类似物，与野生型GIP相比，它们包含一个或多个替换，可能具有改变的性质，最好是增加的GLP-1活性，例如在体外效力实验中评估的那样。本发明提供了GIP-GLP-1双重激动剂化合物及相关方法。
• Application of synthetic liposomes based on acyl amino acids or acyl peptides as drug carriers. I. Their preparation and transport of glutathione into the liver.
  作者：HIROSHI KIWADA、MASAMI AKIMOTO、MICHIYO ARAKI、MITSUKO TSUJI、YURIKO KATO

  DOI：10.1248/cpb.35.2935

  日期：——

  Palmitoyl amino acids and palmitoyl glutathione were synthesized. Liposome-like vesicles based on these compounds were prepared and their barrier functions were examined. These vesicles showed encapsulation efficiencies for aqueous solute comparable to that of conventional phosphatidylcholine liposomes (PC-liposomes). They were also stable in fresh rat plasma at 37°C. The biological behavior (blood clearance, urinary excretion and tissue distribution) of the vesicles based on palmitoyl serine (PSer-liposomes) or palmitoyl glutathione (PGSH-liposomes) was examined after intravenous injection in rats. The synthetic liposomes were cleared very rapidly from the blood compared with PC-liposomes. PSer-Liposomes showed a large amount of urinary excretion of aqueous marker ([3H] inulin), suggesting that the mechanisms of vesicle degradation in vivo and in vitro are different. These synthetic liposomes showed low affinity to the spleen and high affinity to the liver in the tissue distribution study, and thus they may be expected to be a useful drug carrier which is targetable to the liver. A suppressing effect of PGSH-liposomes on the increase of plasma glutamate oxaloacetate transaminase (GOT) induced by a high dose of acetaminophen in mice was observed, and transport of glutathione into the liver cells apparently occurred. The suppressing effect was greater than that of free glutathione or PC-liposomes containing free glutathione. However, the effect was not observed in the case of PGSH-liposomes without phosphatidylcholine, which appears to have an important role in the liposome-cell interaction.

  合成了棕榈酰氨基酸和棕榈酰谷胱甘肽。基于这些化合物的脂质体样囊泡被制备出来，并检测了它们的屏障功能。这些囊泡对水溶性溶质的包封效率与传统磷脂酰胆碱脂质体（PC-脂质体）相当。它们在37°C的新鲜大鼠血浆中也表现稳定。基于棕榈酰丝氨酸（PSer-脂质体）或棕榈酰谷胱甘肽（PGSH-脂质体）的囊泡在大鼠静脉注射后的生物行为（血液清除、尿液排泄和组织分布）被研究。合成脂质体相比PC-脂质体从血液中清除得非常迅速。PSer-脂质体显示出大量的水溶性标记物（[3H]菊粉）的尿液排泄，表明囊泡在体内和体外的降解机制是不同的。这些合成脂质体在组织分布研究中对脾脏的亲和力低，而对肝脏的亲和力高，因此它们可能成为肝脏靶向的有用药物载体。观察到PGSH-脂质体对小鼠因高剂量扑热息痛引起的血浆谷氨酸草酰乙酸转氨酶（GOT）升高的抑制作用，并且明显发生了谷胱甘肽向肝细胞的转运。抑制效果大于游离谷胱甘肽或含有游离谷胱甘肽的PC-脂质体。然而，在没有磷脂酰胆碱的PGSH-脂质体中并未观察到这种效果，这表明磷脂酰胆碱在脂质体-细胞相互作用中起着重要作用。
• 酰胺基羧酸类化合物的制备方法和应用
  申请人：中南大学

  公开号：CN109761837B

  公开（公告）日：2020-05-15

  本发明公开了一种酰胺基羧酸类化合物的制备方法和应用，所述制备方法是将具有式(I)结构的有机羧酸与具有式(II)结构的氨基酸类化合物在偶联试剂存在的条件下经研磨反应制得具有式(III)结构的酰胺基羧酸类化合物，所述方法制备的产品收率高，节能环保且不需后处理；所述应用是将酰胺基羧酸类化合物作为捕收剂在矿物浮选中的应用，捕收剂具有较强的捕收能力和较好的选择性，特别适应于黑钨矿、白钨、稀土矿、锡石、钛铁矿、铝土矿、氧化锰矿、磷矿、萤石矿等矿物的浮选。
• [EN] SYNTHESIS OF LIRAGLUTIDE<br/>[FR] SYNTHÈSE DE LIRAGLUTIDE
  申请人：BIOCON LTD

  公开号：WO2018104922A1

  公开（公告）日：2018-06-14

  The present invention relates to the efficient solid-phase synthesis of liraglutide represented by Formula-I. The present invention relates to an efficient process for the preparation of liraglutide by sequential coupling employing solid phase approach. It involves sequential coupling of protected amino acids to prepare backbone of liraglutide and upon completion of linear sequence, synthesis was extended from lysine side chain by adding γ-glutamic acid and palmitic acid, followed by removal of protective groups, cleavage of the peptide from solid support and purification of crude liraglutide obtained. The present invention also involves the usage of inorganic salts during the coupling, wash with HOBt in DMF solution after Fmoc-deprotection step to suppress the aggregation of peptides and ensure reactions are going for completion, and thus avoid deletion sequences and improve the process yield.

  本发明涉及利拉鲁肽的高效固相合成，其化学式为I。本发明涉及一种采用固相方法进行顺序耦合的高效制备利拉鲁肽的方法。该方法涉及保护氨基酸的顺序耦合以制备利拉鲁肽的骨架，在线性序列完成后，从赖氨酸侧链开始合成，加入γ-谷氨酸和棕榈酸，去除保护基，将肽从固体支持体上裂解并纯化得到粗利拉鲁肽。本发明还涉及在耦合过程中使用无机盐，在Fmoc去保护基步骤后使用DMF溶液中的HOBt进行洗涤，以抑制肽的聚集并确保反应完成，从而避免删除序列并提高工艺产率。
• Regulation of the Chiral Twist and Supramolecular Chirality in Co-Assemblies of Amphiphilic L-Glutamic Acid with Bipyridines
  作者：Xuefeng Zhu、Pengfei Duan、Li Zhang、Minghua Liu

  DOI：10.1002/chem.201002595

  日期：2011.3.14

  π–π stacking, hydrophobic, and chiral interactions is responsible for the formation of the chiral twists. An interesting sandwich structure, in which an excess of 4,4′‐bipyridine is inserted into the space of primary cages constructed from the amphiphile and 4,4′‐bipyridine, is proposed. Remarkably, the handedness of these chiral twists is related not only to the chiral center of the glutamic unit, but

  一系列两亲L‐glutamic acid derivatives with various saturated alkyl chains has been designed and their co‐assembly with 4,4′‐bipyridine in aqueous media has been investigated. While the individual amphiphiles formed hydrogels with water and self‐assembled into fine fiber networks, the addition of 4,4′‐bipyridine caused significant changes in the co‐assembled nanostructures such that twisted chiral ribbons