甲基丙二酰DL-肉碱氯化物

• 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: 甲基丙二酰DL-肉碱氯化物
• 英文名称: methylmalonylcarnitine hydrochloride
• 英文别名: 3-[1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy-2-methyl-3-oxopropanoate;hydrochloride
• 化学式: C₁₁H₂₀NO₆*Cl
• 分子量: 297.736
• InChiKey: GCTKNVUCBFQXAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲基丙二酸亚异丙酯 、 DL-肉碱盐酸盐 在 三氟乙酸 作用下， 反应 18.0h， 生成 甲基丙二酰DL-肉碱氯化物
  参考文献：
  名称：

  二羧酸酰基肉碱的合成。

  摘要：

  描述了丙二酰基，甲基丙二酰基，琥珀酰基，戊二酰基，甲基戊二酰基，十二烷二酰基和十六烷二酰基肉碱的合成。由在三氟乙酸溶液中的八当量的二羧酸的环状酸酐或异亚丙基酯和肉碱氯化物制备二羧酸酰基肉碱。长链二羧酸酰基肉碱还通过在水和正丁醇之间分配进行纯化。还制备了含有3、6或9个氘原子的稳定同位素标记的类似物。它们用作电喷雾离子化串联质谱分析中患有脂肪酸氧化遗传性疾病的患者样品中二羧酸酰基肉碱的标准品。

  DOI：

  10.1016/j.chemphyslip.2004.01.001

文献信息

• Kinetic and molecular orbital analyses of dicarboxylic acylcarnitine methylesterification show that derivatization may affect the screening of newborns by tandem mass spectrometry
  作者：Yasuhiro Maeda、Yoko Nakajima、Kana Gotoh、Yuji Hotta、Tomoya Kataoka、Naruji Sugiyama、Naohiro Shirai、Tetsuya Ito、Kazunori Kimura

  DOI：10.1016/j.bmcl.2015.11.016

  日期：2016.1

  Newborns are routinely screened for organic acidemias by acylcarnitine analysis. We previously reported the partial catalytic methylesterification of dicarboxylic acylcarnitines by benzenesulfonic acid moiety in the solid extraction cartridge during extraction from serum. Since the diagnosis of organic acidemias by tandem mass spectrometry is affected by the higher molecular weight of these derivatized acylcarnitines, we investigated the methylesterification conditions. The kinetic constants for the methylesterification of carboxyl groups on the acyl and carnitine sides of carnitine were 2.5 and 0.24 h (1), respectively. The physical basis underlying this difference in methylesterification rates was clarified theoretically, illustrating that methylesterification during extraction proceeds easily and must be prevented. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of dicarboxylic acylcarnitines
  作者：David W. Johnson

  DOI：10.1016/j.chemphyslip.2004.01.001

  日期：2004.5

  methylglutaryl, dodecanedioyl and hexadecanedioyl carnitines are described. The dicarboxylic acylcarnitines were prepared from eight equivalents of cyclic anhydride or isopropylidene ester of the dicarboxylic acid and carnitine chloride in trifluoroacetic acid solution. Long chain dicarboxylic acylcarnitines were additionally purified by partitioning between water and n-butanol. Stable isotope labeled

  描述了丙二酰基，甲基丙二酰基，琥珀酰基，戊二酰基，甲基戊二酰基，十二烷二酰基和十六烷二酰基肉碱的合成。由在三氟乙酸溶液中的八当量的二羧酸的环状酸酐或异亚丙基酯和肉碱氯化物制备二羧酸酰基肉碱。长链二羧酸酰基肉碱还通过在水和正丁醇之间分配进行纯化。还制备了含有3、6或9个氘原子的稳定同位素标记的类似物。它们用作电喷雾离子化串联质谱分析中患有脂肪酸氧化遗传性疾病的患者样品中二羧酸酰基肉碱的标准品。