N-(十二酰基)-Β-丙氨酸 | 21539-56-0

• 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: N-(十二酰基)-Β-丙氨酸
• 中文别名: 月桂酰Β-氨基丙酸
• 英文名称: N-lauroyl-β-alanine
• 英文别名: Lauroyl beta-alanine；3-(dodecanoylamino)propanoic acid
• CAS: 21539-56-0
• 化学式: C₁₅H₂₉NO₃
• mdl: MFCD00438266
• 分子量: 271.4
• InChiKey: ILKFYYOGOCVZRU-UHFFFAOYSA-N

物化性质

• 熔点：
  93-95 °C
• 沸点：
  461.7±28.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.866
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(十二酰基)-Β-丙氨酸 在 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 4-aza-N-(3-{4-[4-methyl-3,3-bis(propan-2-yl)-3-silapent-1-ynyl]phenyl}prop-2-ynyl)-5-oxohexadecanamide
  参考文献：
  名称：

  Deciphering the potentiometric properties of (porphinato)zinc(ii)-derived supramolecular polymers and related superstructures

  摘要：

  利用电化学测量方法，研究了基于卟啉的超分子聚合物的电位性质。这些自组装材料的结构-功能关系已经被阐明。

  DOI：

  10.1039/c8tc02979b
• 作为产物：
  描述：

  月桂酸甲酯 在 Candida antarctica lipase 、 氢氧化钾 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙二醇甲醚 为溶剂， 反应 171.0h， 生成 N-(十二酰基)-Β-丙氨酸
  参考文献：
  名称：

  有机介质中N-月桂酰-β-丙氨酸同系物的酶促合成

  摘要：

  AbstractEnyzmatic amidation of the primary amines β‐alanine ethyl ester and 3‐aminopropionitrile with methyl laurate by means of immobilized lipase (Candida antarctica lipase, CAL) resulted in the formation in good yield of N‐lauroyl‐β‐alanine ethyl ester and 3‐(N‐lauroylamino)‐propionitrile, respectively. When 3‐amino‐propionitrile was used as substrate, diisopropyl ether was a suitable solvent. Changing the reaction temperature (12–80°C) did not affect the yields, and room temperature was a suitable temperature for this reaction. In the investigation of reaction conditions, the use of equimolar amounts (5 mmol) of substrate and ester, along with 0.5 g of CAL, in diisopropyl ether gave the best yield (99.3%) after 24 h of incubation at 24°C. The enzyme activity in the amidation reaction did not decrease even after six uses. With β‐alanine ethyl ester hydrochloride as substrate, diisopropyl ether was unsuited as a solvent owing to the low solubility of the substrate in this solvent.In this reaction, the best yield (82.0%) was attained by using dioxane as solvent. CAL achieved higher extents of amide synthesis with long‐chain than with short‐chain ester substrates. The enzyme accepted only nonbulky primary amines as substrates.

  DOI：

  10.1007/s11746-997-0231-9

文献信息

• Molecular structural requirements, dye specificity, and application of anionic peptide amphiphiles that induce intense fluorescence in cationic dyes
  作者：Hiroshi Hachisako、Naoya Ryu、Ryoichi Murakami

  DOI：10.1039/b818206j

  日期：——

  acid with relatively shorter side-chain methylenes. The dye specificity in terms of induction of the intense fluorescence was also investigated using hemicyanines (stilbazoliumetc.), cyanine, carbocyanine, thiacarbocyanines, and azo dye. The amphiphile with the shortest octanoyl-β-alanyl double-chain alkyl groups, longer side-chain, and shorter spacer was found to show increased sensitivity to alkali

  我们以前曾报道过，能够在分子间形成三氢键的双链阴离子两亲物可能在水中形成极疏水的位点。 水特别是掺入了基于噻唑鎓的紧凑型半花青染料作为单体物质，从而导致染料中强烈的荧光发射。本文研究了强荧光诱导两亲物的结构要求。注意到将β-Ala残基引入两个长链烷基基团对于衍生自的两亲物最有效L-谷氨酸具有相对较短的侧链亚甲基。还使用半花菁（stilbazolium等），花菁，碳花菁，硫代碳菁和偶氮染料研究了染料在诱导强荧光方面的特异性。发现具有最短的辛酰基-β-丙氨酰基双链烷基，侧链较长和间隔基较短的两亲物显示出对碱金属离子，特别是Li +的敏感性增加。这可能是Li +的潜在OFF-ON型荧光传感器。
• Site-specific effect of polar functional group-modification in lipids of TLR2 ligands for modulating the ligand immunostimulatory activity
  作者：Yohei Arai、Shinsuke Inuki、Yukari Fujimoto

  DOI：10.1016/j.bmcl.2018.03.042

  日期：2018.5

  of TLR2, small polar regions were found in the hydrophobic TLR2 pocket. Interactions between the polar residues and ligands were explored here by designing and synthesizing a Pam2CSK4 derivative of the TLR2 ligands, containing an amide group within the lipid moiety. We evaluated the binding affinities and immunomodulatory activities of these ligands. Results suggested that the amide groups in the lipid

  Toll样受体2（TLR2）是TLR先天性免疫受体家族的成员，它能够识别细菌中的脂蛋白并通过诱导各种细胞因子的表达来调节免疫反应。TLR2有一个大的疏水口袋，可识别TLR2配体上的长脂肪酰基。然而，很少有研究集中在疏水性TLR2袋的性质上。基于TLR2的X射线晶体结构，在疏水性TLR2的口袋中发现了小的极性区域。通过设计和合成Pam 2 CSK 4，探索了极性残基与配体之间的相互作用。TLR2配体的衍生物，在脂质部分包含一个酰胺基。我们评估了这些配体的结合亲和力和免疫调节活性。结果表明脂质链中的酰胺基团与TLR2疏水脂质结合口袋中的极性残基相互作用。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• Formation of unusual side-products from succinimidyl esters of fatty acids during the acylation of amino acids
  作者：Alenka Paquet、Michel Bergeron

  DOI：10.1139/v82-248

  日期：1982.7.15

  A new side-product, succinohydroxamic decanoic anhydride, was isolated from the reaction mixture during the acylation of lysine by succinimidyl decanoate in the presence of aqueous sodium hydroxide. Laurie and palmitic acid derivatives were also obtained. It is shown that these compounds can be used for acylation of amino acids. The hydroxamic acid derivatives were also detected when the acylations by succinimidyl esters of fatty acids were carried out under anhydrous conditions. Preparation of N-lauroyl-L-tyrosine methyl ester from tyrosine methyl ester and succinimidyl laurate is also described.

  一种新的副产物，琥珀酰羟羟胺癸酸酐，在琥珀酰亚胺癸酸酯在水合氢氧化钠存在下与赖氨酸酰基化反应过程中从反应混合物中分离出来。还获得了劳瑞和棕榈酸衍生物。表明这些化合物可用于氨基酸的酰基化。当在无水条件下使用脂肪酸琥珀酰亚胺酯进行酰基化时，也检测到了羟羟胺酸衍生物。还描述了从酪氨酸甲酯和琥珀酰亚胺月桂酸酯制备N-月桂酰-L-酪氨酸甲酯的过程。
• Structure, supramolecular organization and phase behavior of N-acyl-β-alanines: Structural homologues of mammalian brain constituents N-acylglycine and N-acyl-GABA
  作者：D. Sivaramakrishna、Musti J. Swamy

  DOI：10.1016/j.chemphyslip.2016.10.002

  日期：2016.12

  Strong hydrogen bonding interactions between COOH groups of the molecules from opposite leaflets as well as NH⋯O hydrogen bonds between the amide groups from adjacent molecules in the same leaflet as well as dispersion interactions between the acyl chains stabilize the bilayer structure. The d-spacings calculated from powder X-ray diffraction studies showed odd-even alteration with odd-chain length compounds

  Ñ酰基-β-丙氨酸（一个Nabas）是结构同源物Ñ -acylglycines（唠叨）和Ñ酰基-γ氨基酸（NAGABAs），和非手性异构体Ñ -acylalanines，这些都是存在于哺乳动物的脑和其他组织和调节具有各种功能的生物受体的活性。在本研究中，我们合成并表征了一系列带有饱和酰基链的NABA（n = 8-20），并研究了它们的超分子组织和热致相行为。在差示扫描量热（DSC）研究中，大多数NABA在干态主链熔融相变之前以及与水水合时都会发生一两个次要的过渡，但在与缓冲液水合时仅会发生一个过渡（ pH 7.6）。从DSC研究获得的跃迁焓（ΔH t）和熵（ΔS t）显示出在干燥状态和缓冲液水合时对链长的线性依赖性，而在用水水合时观察到奇偶变化。N-月桂酰-β-丙氨酸（NLBA）和N的晶体结构在P21 / c空间群的单斜系统中解决了-肉豆蔻酰基-β-丙氨酸（NMBA）问题。NLBA和NMB