肉豆蔻酰基-L-肉碱 | 25597-07-3

• 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: 肉豆蔻酰基-L-肉碱
• 英文名称: tetradecanoylcarnitine
• 英文别名: myristoylcarnitine；(3R)-3-tetradecanoyloxy-4-(trimethylazaniumyl)butanoate
• CAS: 25597-07-3
• 化学式: C₂₁H₄₁NO₄
• 分子量: 371.561
• InChiKey: PSHXNVGSVNEJBD-LJQANCHMSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜
• 物理描述：
  Solid
• 碰撞截面：
  207.28 Ų [M]+ [CCS Type: TIMS, Method: single field calibrated]

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 储存条件：
  存储条件：2-8°C，干燥，密封。

制备方法与用途

生物活性

十四碳肉毒碱（Tetradecanoylcarnitine）是人体中的肉毒碱，参与长链脂肪酸的β型氧化。

靶点

Human Endogenous Metabolite（人类内源性代谢物）

反应信息

• 作为反应物：
  描述：

  肉豆蔻酰基-L-肉碱 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 myristyl-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 、 myristoyl-CoA(4-) 生成 coenzyme A 、 肉豆蔻酰基-L-肉碱
  参考文献：
  名称：

  肉碱棕榈酰转移酶2：对底物特异性及其对酰基肉碱谱分析的启示。

  摘要：

  近年来，酰基肉碱已成为诊断线粒体脂肪酸β-氧化（mFAO）和支链氨基酸氧化障碍的重要生物标志物，前提是它们反映了潜在的毒性酰基辅酶A物种，在线粒体内积累在酶嵌段的上游。但是，这些中间体的起源仍然知之甚少。肉碱航天飞机成员肉碱棕榈酰转移酶2（CPT2）可能参与了线粒体内由积累的酰基CoA代谢产物合成的酰基肉碱。为了解决这个问题，本文研究了CPT2的底物特异性概况。将表达人CPT2的啤酒酵母匀浆与饱和和不饱和的C2-C26酰基辅酶A和支链氨基酸氧化中间体孵育。通过ESI-MS / MS对产生的酰基肉碱进行定量。我们显示CPT2与中等（C8-C12）和长链（C14-C18）酰基辅酶A酯具有活性，而实际上未发现短链和长链酰基辅酶A或支链氨基具有活性酸氧化中间体。还发现反式-2-烯酰基-CoA中间体是CPT2的不良底物。进行的抑制研究表明，trans-2-C16：1-CoA可以作为CPT2的竞争性抑制剂（K（i）为18

  DOI：

  10.1016/j.bbadis.2010.06.002

文献信息

• [EN] NOVEL CRYSTALLINE FORMS<br/>[FR] NOUVELLES FORMES CRISTALLINES
  申请人：GRUENENTHAL CHEMIE

  公开号：WO2017195031A1

  公开（公告）日：2017-11-16

  Preparation and characterization of novel forms of (1-hydroxy-2-imidazol-1-yl-1-phosphono-ethyl) phosphonic acid, suitable for pharmaceutical compositions in drug delivery systems for humans.

  制备和表征新型(1-羟基-2-咪唑-1-基-1-膦酸乙基)膦酸，适用于人类药物输送系统中的药用组合物。
• Leaky β-Oxidation of a trans-Fatty Acid
  作者：Wenfeng Yu、Xiquan Liang、Regina E. Ensenauer、Jerry Vockley、Lawrence Sweetman、Horst Schulz

  DOI：10.1074/jbc.m409640200

  日期：2004.12

  The degradation of elaidic acid (9-trans-octadecenoic acid), oleic acid, and stearic acid by rat mitochondria was studied to determine whether the presence of a trans double bond in place of a cis double bond or no double bond affects beta-oxidation. Rat mitochondria from liver or heart effectively degraded the coenzyme A derivatives of all three fatty acids. However, with elaidoyl-CoA as a substrate, a major metabolite accumulated in the mitochondrial matrix. This metabolite was isolated and identified as 5-trans-tetradecenoyl-CoA. In contrast, little or none of the corresponding metabolites were detected with oleoyl-CoA or stearoyl-CoA as substrates. A kinetic study of long-chain acyl-CoA dehydrogenase (LCAD) and very long-chain acyl-CoA dehydrogenase revealed that 5-trans-tetradecenoyl-CoA is a poorer substrate of LCAD than is 5-cis-tetradecenoyl-CoA, while both unsaturated acyl-CoAs are poor substrates of very long-chain acyl-CoA dehydrogenase when compared with myristoyl-CoA. Tetradecenoic acid and tetradecenoylcarnitine were detected by gas chromatography/ mass spectrometry and tandem mass spectrometry, respectively, when rat liver mitochondria were incubated with elaidoyl-CoA but not when oleoyl-CoA was the substrate. These observations support the conclusion that 5-trans-tetradecenoyl-CoA accumulates in the mitochondrial matrix, because it is less efficiently dehydrogenated by LCAD than is its cis isomer and that the accumulation of this beta-oxidation intermediate facilitates its hydrolysis and conversion to 5-trans-tetradecenoylcarnitine thereby permitting a partially degraded fatty acid to escape from mitochondria. Analysis of this compromised but functional process provides insight into the operation of beta-oxidation in intact mitochondria.
• Characterization of acylcarnitines using fast atom bombardment mass spectrometry and gas chromatography/mass spectrometry
  作者：J. F. Van Bocxlaer、M. Claeys、H. Van Den Heuvel、A. P. De Leenheer

  DOI：10.1002/jms.1190300112

  日期：1995.1

  Mass spectral data are reported for an extended series of synthesized acylcarnitines. Direct mass spectrometry was performed using ionization by fast atom bombardment in combination with high-energy collisional activation and B/E linked scanning. The data show that it is possible to distinguish between isomeric compounds using this technique. Gas chromatographic/mass spectrometric analysis data for acylcarnitines, as their acyloxylactone derivatives, are reported. Both electron impact and chemical ionization modes were used, permitting the unequivocal characterization and identification of the various compounds. In view of the recent marked increase in acylcarnitine profiling activities, the comprehensively reported mass spectrometric and gas chromatographic data may be useful for reference purposes.

  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。
• Carnitine palmitoyltransferase 2: New insights on the substrate specificity and implications for acylcarnitine profiling
  作者：Sara Violante、Lodewijk IJlst、Henk van Lenthe、Isabel Tavares de Almeida、Ronald J. Wanders、Fátima V. Ventura

  DOI：10.1016/j.bbadis.2010.06.002

  日期：2010.9

  were quantified by ESI-MS/MS. We show that CPT2 is active with medium (C8-C12) and long-chain (C14-C18) acyl-CoA esters, whereas virtually no activity was found with short- and very long-chain acyl-CoAs or with branched-chain amino acid oxidation intermediates. Trans-2-enoyl-CoA intermediates were also found to be poor substrates for CPT2. Inhibition studies performed revealed that trans-2-C16:1-CoA may

  近年来，酰基肉碱已成为诊断线粒体脂肪酸β-氧化（mFAO）和支链氨基酸氧化障碍的重要生物标志物，前提是它们反映了潜在的毒性酰基辅酶A物种，在线粒体内积累在酶嵌段的上游。但是，这些中间体的起源仍然知之甚少。肉碱航天飞机成员肉碱棕榈酰转移酶2（CPT2）可能参与了线粒体内由积累的酰基CoA代谢产物合成的酰基肉碱。为了解决这个问题，本文研究了CPT2的底物特异性概况。将表达人CPT2的啤酒酵母匀浆与饱和和不饱和的C2-C26酰基辅酶A和支链氨基酸氧化中间体孵育。通过ESI-MS / MS对产生的酰基肉碱进行定量。我们显示CPT2与中等（C8-C12）和长链（C14-C18）酰基辅酶A酯具有活性，而实际上未发现短链和长链酰基辅酶A或支链氨基具有活性酸氧化中间体。还发现反式-2-烯酰基-CoA中间体是CPT2的不良底物。进行的抑制研究表明，trans-2-C16：1-CoA可以作为CPT2的竞争性抑制剂（K（i）为18