hexadecanedioate

• 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: hexadecanedioate
• 英文别名: HDA
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: QQHJDPROMQRDLA-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hexadecanedioate 在 三甲基乙酸 作用下， 生成 hydrogen hexadecanedioate
  参考文献：
  名称：

  质子从羧酸转移到二价阴离子的速率、CO2(CH2)pCO22- 及其对在气相中观察到的蛋白质负电荷状态的意义

  摘要：

  羧酸双阴离子 CO 2 (CH 2 ) p CO 2 2 - 是两个去质子化酸性侧链（例如 Glu 或 Asp）的最简单模型，它们位于非变性球状蛋白的相对两侧。电荷还原反应的速率常数测定，CO 2 (CH 2 ) p CO 2 2 - + AH = HCO 2 (CH 2 ) p CO 2 - + A - ，涉及具有 C n 的双阴离子，其中 n 范围为 7 至 16 ( n = p + 2) 与包括乙酸在内的各种含氧酸 AH 表明，对于所有上述试剂，电荷减少（损失）发生在碰撞速率下。这与带正电荷的蛋白质的结果相反。模型反应中碰撞速率下的电荷损失（对于两个赖氨酸侧链）NH 3 + H 3 N(CH 2 ) p NH 3 2 + = NH 3 (CH 2 ) p NH 2 + + NH 4 + 仅发生对于 C n 当 n < 7 (n = p)。这些结果解释了在负离子模式下非变性蛋白质的较低

  DOI：

  10.1021/jp021326s
• 作为产物：
  描述：

  水 、 hexadecanedioyl-CoA 生成 coenzyme A 、 氢(+1)阳离子 、 hexadecanedioate
  参考文献：
  名称：

  A role for the human peroxisomal half-transporter ABCD3 in the oxidation of dicarboxylic acids

  摘要：

  Peroxisomes play a major role in human cellular lipid metabolism, including fatty acid beta-oxidation. Free fatty acids (FFAs) can enter peroxisomes through passive diffusion or by means of ATP binding cassette (ABC) transporters, including HsABCD1 (ALDP, adrenoleukodystrophy protein), HsABCD2 (ALDRP) and HsABCD3 (PMP70). The physiological functions of the different peroxisomal half-ABCD transporters have not been fully determined yet, but there are clear indications that both HsABCD1 and HsABCD2 are required for the breakdown of fatty acids in peroxisomes. Here we report that the phenotype of the pxa1/pxa2 Delta yeast mutant, i.e. impaired oxidation of oleic acid, cannot only be partially rescued by HsABCD1, HsABCD2, but also by HsABCD3, which indicates that each peroxisomal half-transporter can function as homodimer. Fatty acid oxidation measurements using various fatty acids revealed that although the substrate specificities of HsABCD1, HsABCD2 and HsABCD3 are overlapping, they have distinctive preferences. Indeed, most hydrophobic C24:0 and C26:0 fatty acids are preferentially transported by HsABCD1, C22:0 and C22:6 by HsABCD2 and most hydrophilic substrates like long-chain unsaturated-, long branched-chain- and long-chain dicarboxylic fatty acids by HsABCD3. All these fatty acids are most likely transported as CoA esters. We postulate a role for human ABCD3 in the oxidation of dicarboxylic acids and a role in buffering fatty acids that are overflowing from the mitochondrial beta-oxidation system. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbalip.2013.12.001

文献信息

• The microsomal dicarboxylyl-CoA synthetase
  作者：J Vamecq、E de Hoffmann、F Van Hoof

  DOI：10.1042/bj2300683

  日期：1985.9.15

  Dicarboxylic acids are products of the omega-oxidation of monocarboxylic acids. We demonstrate that in rat liver dicarboxylic acids (C5-C16) can be converted into their CoA esters by a dicarboxylyl-CoA synthetase. During this activation ATP, which cannot be replaced by GTP, is converted into AMP and PPi, both acting as feedback inhibitors of the reaction. Thermolabile at 37 degrees C, and optimally active at pH 6.5, dicarboxylyl-CoA synthetase displays the highest activity on dodecanedioic acid (2 micromol/min per g of liver). Cell-fractionation studies indicate that this enzyme belongs to the hepatic microsomal fraction. Investigations about the fate of dicarboxylyl-CoA esters disclosed the existence of an oxidase, which could be measured by monitoring the production of H2O2. In our assay conditions this H2O2 production is dependent on and closely follows the CoA consumption. It appears that the chain-length specificity of the handling of dicarboxylic acids by this catabolic pathway (activation to acyl-CoA and oxidation with H2O2 production) parallels the pattern of the degradation of exogenous dicarboxylic acids in vivo.

  二羧酸是单羧酸的ω-氧化产物。我们证明在大鼠肝脏中，二羧酸（C5-C16）可以通过二羧酰辅酶A合成酶转化为它们的CoA酯。在此激活过程中，ATP不能被GTP所替代，会被转化为AMP和PPi，二者均作为反馈抑制剂。二羧酰辅酶A合成酶在37摄氏度下热敏，最适活性pH为6.5，对十二烷二酸的活性最高（每克肝2微摩尔/分钟）。细胞分离研究表明，该酶属于肝微粒体部分。关于二羧酰辅酶A酯的命运的研究揭示了存在一种氧化酶，可以通过监测H2O2产生来测量。在我们的实验条件下，这种 产生依赖于并紧随CoA的消耗。似乎，这种分解途径对二羧酸的链长特异性（激活为酰CoA和 产生的氧化）与体内外源性二羧酸降解的模式相似。