(S)-3'-hydroxybutanoyl-(R)-carnitine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3'-hydroxybutanoyl-(R)-carnitine
• 英文别名: (S)-3-hydroxybutyryl carnitine
• 化学式: C₁₁H₂₁NO₅
• 分子量: 247.291
• InChiKey: UEFRDQSMQXDWTO-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.48
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  86.66
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  、 左旋肉碱盐酸盐 在 三氯乙酸 作用下， 反应 18.0h， 生成 (S)-3'-hydroxybutanoyl-(R)-carnitine
  参考文献：
  名称：

  An LC-MS/MS method to quantify acylcarnitine species including isomeric and odd-numbered forms in plasma and tissues

  摘要：

  Acylcarnitines are intermediates of fatty acid and amino acid oxidation found in tissues and body fluids. They are important diagnostic markers for inherited diseases of peroxisomal and mitochondrial oxidation processes and were recently described as biomarkers of complex diseases like the metabolic syndrome. Quantification of acylcarnitine species can become challenging because various species occur as isomers and/or have very low concentrations. Here we describe a new LC-MS/MS method for quantification of 56 acylcarnitine species with acyl-chain lengths from C2 to C18. Our method includes amino acid-derived positional isomers, like methacrylyl-carnitine (2-M-C3:1-CN) and crotonyl-carnitine (C4:1-CN), and odd-numbered carbon species, like pentadecanoyl-carnitine (C15:0-CN) and heptadecanoyl-carnitine (C17:0-CN), occurring at very low concentrations in plasma and tissues. Method validation in plasma and liver samples showed high sensitivity and excellent accuracy and precision. In an application to samples from streptozotocin-treated diabetic mice, we identified significantly increased concentrations of acylcarnitines derived from branched-chain amino acid degradation and of odd-numbered straight-chain species, recently proposed as potential biomarkers for the metabolic syndrome. In conclusion, the LC-MS/MS method presented here allows robust quantification of isomeric acylcarnitine species and extends the palette of acylcarnitines with diagnostic potential derived from fatty acid and amino acid metabolism.

  DOI：

  10.1194/jlr.d061721

文献信息

• Carnitine-esters from the mushroom Suillus laricinus
  作者：Hirokazu Kawagishi、Hiroaki Murakami、Shingo Sakai、Shintaro Inoue

  DOI：10.1016/j.phytochem.2006.09.014

  日期：2006.12

  Carnitine-esters (1-8) including, (R)-3-hydroxybutanoyl-(R)-carnitine (5), were isolated from the mushroom Suillus laricinus. Their structures were determined by spectroscopic analyses and by total synthesis. One of these, (R)-3-hydroxy-2-methylpropanoyl-(R)-carnitine (4), promoted hyaluronan-degradation by human skin fibroblasts. (c) 2006 Elsevier Ltd. All rights reserved.
• An LC-MS/MS method to quantify acylcarnitine species including isomeric and odd-numbered forms in plasma and tissues
  作者：Pieter Giesbertz、Josef Ecker、Alexander Haag、Britta Spanier、Hannelore Daniel

  DOI：10.1194/jlr.d061721

  日期：2015.10

  Acylcarnitines are intermediates of fatty acid and amino acid oxidation found in tissues and body fluids. They are important diagnostic markers for inherited diseases of peroxisomal and mitochondrial oxidation processes and were recently described as biomarkers of complex diseases like the metabolic syndrome. Quantification of acylcarnitine species can become challenging because various species occur as isomers and/or have very low concentrations. Here we describe a new LC-MS/MS method for quantification of 56 acylcarnitine species with acyl-chain lengths from C2 to C18. Our method includes amino acid-derived positional isomers, like methacrylyl-carnitine (2-M-C3:1-CN) and crotonyl-carnitine (C4:1-CN), and odd-numbered carbon species, like pentadecanoyl-carnitine (C15:0-CN) and heptadecanoyl-carnitine (C17:0-CN), occurring at very low concentrations in plasma and tissues. Method validation in plasma and liver samples showed high sensitivity and excellent accuracy and precision. In an application to samples from streptozotocin-treated diabetic mice, we identified significantly increased concentrations of acylcarnitines derived from branched-chain amino acid degradation and of odd-numbered straight-chain species, recently proposed as potential biomarkers for the metabolic syndrome. In conclusion, the LC-MS/MS method presented here allows robust quantification of isomeric acylcarnitine species and extends the palette of acylcarnitines with diagnostic potential derived from fatty acid and amino acid metabolism.