L-亮氨酸,N-(1-羰基十二基)- | 14379-40-9

• 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: L-亮氨酸,N-(1-羰基十二基)-
• 英文名称: N-n-dodecanoyl (L)-leucine
• 英文别名: N-dodecanoyl-L-leucine；N-lauroyl-L-leucine；N-dodecanoyl-leucine*；N-(1-Oxododecyl)-L-leucine；(2S)-2-(dodecanoylamino)-4-methylpentanoic acid
• CAS: 14379-40-9
• 化学式: C₁₈H₃₅NO₃
• 分子量: 313.481
• InChiKey: CDOCNWRWMUMCLP-INIZCTEOSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  482.0±28.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  L-亮氨酸,N-(1-羰基十二基)- 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-<4-Deoxy-4-(dodecanoyl-L-leucyl)amino-L-glycero-β-L-manno-heptopyranosylamino>-9H-purine
  参考文献：
  名称：

  Synthesis and Antitumor Activities of Glycine-exchanged Analogs of Spicamycin.

  摘要：

  合成了一系列SPM VIII的类似物，以研究氨基酸部分对抗肿瘤活性的影响。L-苏氨酸类似物和甘氨酸甘氨酸类似物对P388小鼠白血病细胞的细胞毒性明显高于SPM VIII（IC50分别为5.8 nM和0.11 nM，而SPM VIII的IC50为25 nM）。然而，用其他氨基酸替代甘氨酸部分则显著降低了对COL-1人结肠癌异种移植模型的抗肿瘤活性。这项研究表明SPM VIII的甘氨酸部分对抗肿瘤效果至关重要。

  DOI：

  10.7164/antibiotics.48.504
• 作为产物：
  描述：

  L-亮氨酸甲酯盐酸盐 在 sodium hydroxide 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 7.0h， 生成 L-亮氨酸,N-(1-羰基十二基)-
  参考文献：
  名称：

  Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids

  摘要：

  A variety of fatty acid amides of different naturally occurring L-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them L-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.028

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））。
• Salt complexes of two-component N-acylamino acid diastereoisomers: self-assembly studies and modulation of gelation abilities
  作者：Frederic Delbecq、Yuki Masuda、Yuki Ogue、Takeshi Kawai

  DOI：10.1016/j.tetlet.2012.09.107

  日期：2012.11

  The self-assemblies and gelation of various organic solvents by salt complexes of two-component N-acylamino acid diastereoisomers are described. The potent organogelator, N-(2-aminoethyl)-α-[-(1-oxoheptadecyl)amino]phenyl) propanamide, was mixed with various N-acyl leucines having different fatty alkyl chain lengths at a ratio of 1:1. In some cases, their complexation resulted in modulations of the

  描述了通过二组分N-酰基氨基酸非对映异构体的盐配合物的各种有机溶剂的自组装和凝胶化。将有效的有机胶凝剂N-（2-氨基乙基）-α-[-（1-氧代十七烷基）氨基]苯基]丙酰胺与具有不同脂肪烷基链长的各种N-酰基亮氨酸以1：1的比例混合。在某些情况下，它们的络合导致当前胶凝能力的调节。当使用有机胶凝剂的L型进行混合时，胶凝能力似乎与N的疏水性无关-酰基亮氨酸。当使用有机胶凝剂的外消旋体形式时，未观察到这一点。此外，观察到芳族溶剂中的最小胶凝浓度（MGC）以及胶凝能力的改善，例如在水中形成坚固的水凝胶，碳酸R-丙二酯的胶凝和吡啶的意外胶凝。超分子凝胶通过傅立叶变换红外（FT-IR），1 H核磁共振（NMR）光谱学和流变学分析进行分析。相变温度（T g–s）是使用差示扫描量热法（DSC）确定的。通过场发射扫描显微镜（FE-SEM）和透射电子显微镜（TEM）观察到凝胶网络的均质性。薄层结构通过X射线衍射（XRD）确认。
• METHOD FOR PRODUCTION OF L-LYSINE USING METHANOL-UTILIZING BACTERIUM
  申请人：Gunji Yoshiya

  公开号：US20100190216A1

  公开（公告）日：2010-07-29

  A method for production of L-lysine is provided which includes the steps of cultivating a methanol-utilizing bacterium in a culture medium to produce and accumulate L-lysine in the culture medium and collecting the L-lysine from the culture medium, wherein the methanol-utilizing bacterium contains DNA encoding dihydrodipicolinate synthetase which is desensitized to feedback inhibition by L-lysine and DNA encoding a LysE protein that can enhance the excretion of L-lysine out of the methanol-utilizing bacterium, and the bacterium is modified so as to increase the intracellular activities of diaminopimelic acid dehydrogenase, diaminopimelic acid decarboxylase, dihydrodipicolinic acid reductase and aspartate-semialdehyde dehydrogenase.

  提供了一种生产L-赖氨酸的方法，包括以下步骤：在培养基中培养甲醇利用的细菌，以在培养基中产生和积累L-赖氨酸，并从培养基中收集L-赖氨酸。其中，甲醇利用的细菌包含编码对L-赖氨酸反馈抑制不敏感的二氢二氢吡啶酸合成酶的DNA和编码可以增强L-赖氨酸从甲醇利用的细菌中排出的LysE蛋白的DNA，并且对细菌进行改造，以增加二氨基戊二酸脱氢酶、二氨基戊二酸脱羧酶、二氢二氢吡啶酸还原酶和天冬氨酸半醛脱氢酶的细胞内活性。
• Method for Producing an L-Amino Acid
  申请人：AJINOMOTO CO., INC.

  公开号：US20130084609A1

  公开（公告）日：2013-04-04

  An L-amino acid is produced by culturing a bacterium having an L-amino acid-producing ability in a medium containing a processed product of a microalga which promotes production and accumulation of the L-amino acid by the bacterium. The process product is produced by disrupting the culture of the microalga, and/or extracting the culture of the microalga, or fractionating the culture of the microalga or the disrupted culture. The processed product contains a mixture of organic substances produced by the microalga, a hydrolysate of the disrupted microalga culture, and/or an extract or fractionation product of the microalga culture. The processed product can also contain a saccarification product of starch or a hydrolysate of fats and oils. The bacterium is cultured to produce and accumulate the L-amino acid in culture, and the L-amino acid is collected from the culture.

  通过在含有处理过的微藻产物的培养基中培养具有L-氨基酸产生能力的细菌，可以生产出L-氨基酸。处理过的微藻产物通过破坏微藻的培养物、提取微藻的培养物或分离微藻的培养物或破坏培养物的混合物来生产。处理过的产物包含微藻产生的有机物混合物、破坏的微藻培养物的水解产物和/或微藻培养物的提取物或分离产物。处理过的产物还可以包含淀粉的糖化产物或脂肪和油的水解产物。细菌在培养基中培养以产生和积累L-氨基酸，并从培养物中收集L-氨基酸。