(3R)-3-(己酰氧基)-4-(三甲基铵基)丁酸酯 | 22671-29-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (3R)-3-(己酰氧基)-4-(三甲基铵基)丁酸酯
• 英文名称: hexanoylcarnitine
• 英文别名: hexanoyl-L-carnitine；L-Hexanoylcarnitine；(3R)-3-hexanoyloxy-4-(trimethylazaniumyl)butanoate
• CAS: 22671-29-0
• 化学式: C₁₃H₂₅NO₄
• 分子量: 259.346
• InChiKey: VVPRQWTYSNDTEA-LLVKDONJSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性方面，L-Hexanoylcarnitine 是一种酰基肉碱，并与乳糜泻有关。靶点为人类内源性代谢物：Human Endogenous Metabolite。

反应信息

• 作为反应物：
  描述：

  (3R)-3-(己酰氧基)-4-(三甲基铵基)丁酸酯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 hexanoyl-L-carnitine oxylactone
  参考文献：
  名称：

  Characterization of acylcarnitines using fast atom bombardment mass spectrometry and gas chromatography/mass spectrometry

  摘要：

  报告了一系列合成酰基肉碱的质谱数据。采用快速原子轰击离子化技术结合高能碰撞激发和B/E连扫的直接质谱方法。数据显示，可以使用该技术区分异构化合物。报告了以酰氧乳酸酯衍生物形式的酰基肉碱的气相色谱/质谱分析数据。使用了电子轰击和化学电离两种模式，这使得各种化合物的特征和鉴定变得明确无误。鉴于最近酰基肉碱分析活动的显著增加，详细报告的质谱和气相色谱数据可能对参考目的有所帮助。

  DOI：

  10.1002/jms.1190300112
• 作为产物：
  描述：

  左旋肉碱 、 hexanoyl-CoA(4-) 生成 coenzyme A 、 (3R)-3-(己酰氧基)-4-(三甲基铵基)丁酸酯
  参考文献：
  名称：

  Substrate specificity of human carnitine acetyltransferase: Implications for fatty acid and branched-chain amino acid metabolism

  摘要：

  Carnitine acyltransferases catalyze the reversible conversion of acyl-CoAs into acylcarnitine esters. This family includes the mitochondrial enzymes carnitine palmitoyltransferase 2 (CPT2) and carnitine acetyltransferase (CrAT). CPT2 is part of the carnitine shuttle that is necessary to import fatty acids into mitochondria and catalyzes the conversion of acylcarnitines into acyl-CoAs. In addition, when mitochondrial fatty acid P-oxidation is impaired, CPT2 is able to catalyze the reverse reaction and converts accumulating long- and medium-chain acyl-CoAs into acylcarnitines for export from the matrix to the cytosol. However, CPT2 is inactive with short-chain acyl-CoAs and intermediates of the branched-chain amino acid oxidation pathway (BCAAO). In order to explore the origin of short-chain and branched-chain acylcarnitines that may accumulate in various organic acidemias, we performed substrate specificity studies using purified recombinant human CrAT. Various saturated, unsaturated and branched-chain acyl-CoA esters were tested and the synthesized acylcarnitines were quantified by ESI-MS/MS. We show that CrAT converts short- and medium-chain acyl-CoAs (C2 to C10-00A), whereas no activity was observed with long-chain species. Trans-2-enoyl-00A intermediates were found to be poor substrates for this enzyme. Furthermore, CrAT turned out to be active towards some but not all the BCAAO intermediates tested and no activity was found with dicarboxylic acyl-CoA esters. This suggests the existence of another enzyme able to handle the acyl-CoAs that are not substrates for CrAT and CPT2, but for which the corresponding acylcarnitines are well recognized as diagnostic markers in inborn errors of metabolism. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbadis.2013.02.012

文献信息

• Acyl carnitine esterase, production thereof and method for analyzing acyl carnitines
  申请人：ASAHI KASEI KOGYO KABUSHIKI KAISHA

  公开号：EP0480676A2

  公开（公告）日：1992-04-15

  An acylcarnitine esterase which has a substrate specificity to acyl-L-carnitines including short chain acyl-L-carnitines inclusive of acetyl-L-carnitine and propionyl-L-carnitine and which catalyzes the hydrolysis reaction of one mole of the acyl-L-carnitines with one mole of water to form one mole of the corresponding fatty acid and one mole of L-carnitine.

  一种酰基肉碱酯酶，它对酰基-L-肉碱（包括乙酰基-L-肉碱和丙酰基-L-肉碱在内的短链酰基-L-肉碱）具有底物特异性，可催化一摩尔酰基-L-肉碱与一摩尔水的水解反应，生成一摩尔相应的脂肪酸和一摩尔 L-肉碱。
• Use of propionyl L-carnitine for regaining muscle tone in immobilised patients
  申请人：SIGMA TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0517125A1

  公开（公告）日：1992-12-09

  The oral or parenteral administration of acyl L-carnitine, for example of propionyl L-carnitine (10-30 mg/Kg of body weight/day), allows rapid regain of muscle tone in patients suffering long periods of immobilisation, for example patients with fractures.

  口服或肠道外注射酰基左旋肉碱，例如丙酰左旋肉碱（10-30 毫克/千克体重/天），可使长期固定的患者（如骨折患者）迅速恢复肌肉张力。
• APPARATUS FOR DIAGNOSING SOLID CANCERS AND METHOD FOR PROVIDING INFORMATION ON SOLID CANCER DIAGNOSIS
  申请人：Innobation Bio Co., Ltd.

  公开号：EP4027139A2

  公开（公告）日：2022-07-13

  The present invention relates to an apparatus for diagnosing solid cancers comprising lung cancer, pancreatic cancer, bile duct cancer, colorectal cancer, breast cancer, gastric cancer, brain tumors, kidney cancer, liver cancer, and cervical cancer. More specifically, the apparatus comprises: a concentration measurement unit for measuring the concentration of each of acyl-carnitine (AC), nudifloramide (2PY), and lysophosphatidylcholine (LPC) from a biological sample; a pre-processing unit for pre-processing the measured concentrations; and a diagnosis unit for determining the diagnosis information of cancer through linear discriminant analysis using the pre-processed concentrations.

  本发明涉及一种诊断实体癌的仪器，包括肺癌、胰腺癌、胆管癌、结直肠癌、乳腺癌、胃癌、脑肿瘤、肾癌、肝癌和宫颈癌。更具体地说，该装置包括：浓度测量单元，用于测量生物样本中酰基肉碱（AC）、裸花胺（2PY）和溶血磷脂酰胆碱（LPC）各自的浓度；预处理单元，用于对测量的浓度进行预处理；以及诊断单元，用于使用预处理的浓度通过线性判别分析确定癌症诊断信息。
• Detection method for quaternary ammonium compound having γ-carboxyl group
  申请人：Kaohsiung Medical University

  公开号：US10703969B2

  公开（公告）日：2020-07-07

  A detection method for a quaternary ammonium compound having a γ-carboxyl group includes: mixing a sample including the quaternary ammonium compound having the γ-carboxyl group, a fluorescent compound having a fluorophore and a polar aprotic solvent to form a reaction solution. A SN2 nucleophilic substitution reaction is performed between the fluorophore of the fluorescent compound and the γ-carboxyl group of the quaternary ammonium compound to obtain a derivation solution including a derivative which is a quaternary ammonium compound with the γ-carboxyl group substituted with the fluorophore of the fluorescent compound. An extractant and a cosolvent are added to the derivation solution to form a water-in-oil emulsion which disperses in the derivation solution, followed by extracting the derivative from the derivation solution by the extractant to obtain an analytic solution, wherein a polarity of the extractant is higher than a polarity of the polar aprotic solvent. The derivative in the analytic solution is detected; and therefore, the quaternary ammonium compound having the γ-carboxyl group in the sample can be easily detected by reverse-phase liquid chromatography, fluorescence spectrometry or mass spectrometry.

  一种具有γ-羧基的季铵盐化合物的检测方法包括：将包括具有γ-羧基的季铵盐化合物的样品、具有荧光团的荧光化合物和极性钝化溶剂混合形成反应溶液。在荧光化合物的荧光团和季铵盐化合物的γ-羧基之间进行 SN2 亲核取代反应，以获得衍生物溶液，其中包括一种衍生物，该衍生物是γ-羧基被荧光化合物的荧光团取代的季铵盐化合物。在衍生溶液中加入萃取剂和共溶剂，形成油包水型乳液，分散在衍生溶液中，然后用萃取剂从衍生溶液中萃取衍生物，得到分析溶液，其中萃取剂的极性高于极性钝化溶剂的极性。分析溶液中的衍生物可被检测出来；因此，样品中具有γ-羧基的季铵化合物可以很容易地通过反相液相色谱法、荧光光谱法或质谱法检测出来。
• Detection kit for quaternary ammonium compound having γ-carboxyl group
  申请人：Kaohsiung Medical University

  公开号：US11016096B2

  公开（公告）日：2021-05-25

  The invention discloses a detection kit for a quaternary ammonium compound having a γ-carboxyl group. The kit includes a fluorescent compound having a fluorophore. The fluorophore of the fluorescent compound is used for forming a derivative with the γ-carboxyl group of the quaternary ammonium compound by an SN2 nucleophilic substitution reaction. The kit further includes a polar aprotic solvent used for accelerating the SN2 nucleophilic substitution reaction.

  本发明公开了一种具有γ-羧基的季铵盐化合物的检测试剂盒。该试剂盒包括一种具有荧光团的荧光化合物。荧光化合物的荧光团用于通过 SN2 亲核取代反应与季铵盐化合物的 γ 羧基形成衍生物。试剂盒还包括一种极性钝化溶剂，用于加速 SN2 亲核取代反应。