(R)-2-dodecanamidopropanoic acid | 60654-16-2

• 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
• 英文名称: (R)-2-dodecanamidopropanoic acid
• 英文别名: N-lauroyl-D-alanine；N-lauroyl-D-alanine；N-Lauroyl-D-alanin；N-Dodecanoyl-D-alanine；(2R)-2-(dodecanoylamino)propanoic acid
• CAS: 60654-16-2
• 化学式: C₁₅H₂₉NO₃
• 分子量: 271.4
• InChiKey: UYTOHYBIBPDOKX-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  (R)-2-dodecanamidopropanoic acid 在 硫酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 36.08h， 生成
  参考文献：
  名称：

  Azobenzene coupled chromogenic receptors for the selective detection of copper(II) and its application as a chemosensor kit

  摘要：

  Azobenzene-based receptors 1-4 as colorimetric sensing materials were synthesized and their sensing properties were examined. In solution, the proposed sensing materials give rise to a large cation-induced hypochromic shift for Cu2+ resulting in a change from red to pale-yellow, whereas no significant color change was observed upon addition of other selected metal ions. The use of the silica gel plate modified with immobilization of receptor 4 to detect Cu2+ was also reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.066
• 作为产物：
  描述：

  N-dodecanoyl-DL-α-alanine 生成 (R)-2-dodecanamidopropanoic acid
  参考文献：
  名称：

  DE814296

  摘要：

  公开号：

文献信息

• Enantioselective hydrolysis of long chain α-amino acid esters by chiral sulfur-containing macrocyclic metallomicelles
  作者：Jingsong You、Xiaoqi Yu、Xingshu Li、Qianshun Yan、Rugang Xie

  DOI：10.1016/s0957-4166(98)00098-6

  日期：1998.4

  A novel chiral lipophilic sulfur-containing macrocyclic ligand 5 with bis-pendant alcohols in the proximity of the coordination center has been synthesized. Its metal ion complexes have been investigated as catalysts for the enantioselective hydrolysis of long chain α-amino acid esters in aqueous comicellar solution with Brij35. Large rate accelerations (up to 220 times) and moderate enantioselectivities

  合成了在配位中心附近具有双侧链醇的新型手性亲脂性含硫大环配体5。已经研究了其金属离子络合物作为催化剂在Brij35水溶液中对长链α-氨基酸酯进行对映选择性水解的方法。已经观察到使用大环5- Cu 2+的大速率加速（高达220倍）和中等对映选择性（高达4.85（k S / k R）），而无环3- Cu 2+表现出较低的反应性和立体选择性。取类似的配体4，缺少羟基会导致速率急剧下降，并且观察到对映选择性反转。在我们的胶束反应条件下，与Cu 2+结合的羟基的pKa值确定为pKa = 7.2。
• Synthesis of novel chiral lipophilic pyridyl-containing β-amino alcohol ligands and enantioselective hydrolysis of α-amino acid esters by chiral metallomicelles
  作者：Jingsong You、Xiaoqi Yu、Ke Liu、Lin Tao、Qingxiang Xiang、Rugang Xie

  DOI：10.1016/s0957-4166(98)00512-6

  日期：1999.1

  Seven novel chiral lipophilic pyridyl-containing β-amino alcohol ligands have been synthesized by coupling of 6-alkoxymethyl-2-chloromethylpyridine 3 with the corresponding chiral β-amino alcohols or l-cysteine. Their metal ion complexes have been investigated as catalysts for the enantioselective hydrolysis of N-protected α-amino acid esters in aqueous comicellar solution. The results indicate that

  通过将6-烷氧基甲基-2-氯甲基吡啶3与相应的手性β-氨基醇或1-半胱氨酸偶联，已经合成了七个新颖的手性亲脂性吡啶基含β-氨基醇配体。已经研究了它们的金属离子配合物作为催化剂，用于在漫画溶液中对N-保护的α-氨基酸酯进行对映选择性水解。结果表明，底物与金属催化剂之间的疏水相互作用，配体的刚度，配体的羟基充当亲酰基化的酰基转移过程以及胶束微环境是影响活性和对映选择性的重要因素。大速率加速度（高达三个数量级）和中等对映选择性（高达7.81（k已经观察到采用4a -Cu 2+的R / k S））。
• Inhibition of Human α-Methylacyl CoA Racemase (AMACR): a Target for Prostate Cancer
  作者：Andrew J. Carnell、Ralph Kirk、Matthew Smith、Shane McKenna、Lu-Yun Lian、Robert Gibson

  DOI：10.1002/cmdc.201300179

  日期：2013.8.8

  The enzyme α‐methylacyl CoA racemase (AMACR) is involved in the metabolism of branched‐chain fatty acids and has been identified as a promising therapeutic target for prostate cancer. By using the recently available human AMACR from HEK293 kidney cell cultures, we tested a series of new rationally designed inhibitors to determine the structural requirements in the acyl component. An N‐methylthiocarbamate

  α-甲基酰基辅酶A外消旋酶（AMACR）参与支链脂肪酸的代谢，已被确定为前列腺癌的有希望的治疗靶标。通过使用最近从HEK293肾细胞培养物中获得的人AMACR，我们测试了一系列新的合理设计的抑制剂，以确定酰基成分的结构要求。一种N-甲基硫代氨基甲酸酯（K i = 98 n M），旨在模拟拟议的酶结合的烯醇酸酯，被发现是迄今为止报道的最有效的AMACR抑制剂。
• [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。
• Effects of Different Chain Lengths and Chiral Branched Amino Acids on the Synthesis of Mesoporous Silica
  作者：Haitao Liu、Yuxiang Yang、Lu Liu、Hongming Yuan、Cheng Chen、Xiangnong Liu

  DOI：10.1166/jnn.2014.8667

  日期：2014.7.1

  Ordered mesoporous silica was successfully synthesized by using different chain-length chiral anionic surfactants, N-acylalanine and N-acylvaline as templates, and N-trimethoxy silylpropyl-N, N, N-trimethyl ammonium (TMAPS) as a co-structure-directing agent (CSDA) under weakly acidic conditions. The synthesized products were characterized by X-ray diffraction, scanning electron microscopy, transmission

  以不同链长的手性阴离子表面活性剂，N-酰基丙氨酸和N-酰基缬氨酸为模板，N-三甲氧基甲硅烷基丙基-N，N，N-三甲基铵（TMAPS）作为共结构导向成功地合成了有序介孔二氧化硅弱酸性条件下的抗氧化剂（CSDA）。通过X射线衍射，扫描电子显微镜，透射电子显微镜和氮吸附分析来表征合成的产物。在TMAPS / N-酰基丙氨酸系统中，中间相首先从3D无序结构变为3D六边形结构，最后变为具有增加的阴离子表面活性剂疏水链长度的3D立方结构。但是在TMAPS / N-酰基缬氨酸系统中，中间相首先变成了二维六边形结构，最后变成带有螺旋孔道的3D六边形结构的介孔二氧化硅。还讨论了孔径，表面积和孔体积随链长的变化。