[1,2-¹³C]acetyl-CoA | 140701-77-5

• 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: [1,2-¹³C]acetyl-CoA
• 英文别名: acetyl-CoA；[1,2-(13)C2]acetyl-CoA；[(13)C2]acetyl-CoA；S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (1,2-13C2)ethanethioate
• CAS: 140701-77-5
• 化学式: C₂₃H₃₈N₇O₁₇P₃S
• 分子量: 811.557
• InChiKey: ZSLZBFCDCINBPY-IOYRSMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  51
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  389
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  草酰乙酸 、 [1,2-¹³C]acetyl-CoA 在 si-citrate synthase 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  由耐底物石油杆菌素生物合成酶 AsbA 催化的柠檬酸的对映选择性去对称化。

  摘要：

  AsbA 通过 ATP 依赖的亚精胺缩合催化柠檬酸的高度对映选择性去对称化，以及柠檬酸与几种亚精胺类似物的缩合以及柠檬酸类似物三羧酸与亚精胺的缩合，表明它可能是一种有用的生物催化剂用于不对称合成。

  DOI：

  10.1039/b823147h
• 作为产物：
  描述：

  乙酸-13C2 、 辅酶 A 在 acetyl-CoA synthetase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 反应 0.5h， 生成 [1,2-¹³C]acetyl-CoA
  参考文献：
  名称：

  由耐底物石油杆菌素生物合成酶 AsbA 催化的柠檬酸的对映选择性去对称化。

  摘要：

  AsbA 通过 ATP 依赖的亚精胺缩合催化柠檬酸的高度对映选择性去对称化，以及柠檬酸与几种亚精胺类似物的缩合以及柠檬酸类似物三羧酸与亚精胺的缩合，表明它可能是一种有用的生物催化剂用于不对称合成。

  DOI：

  10.1039/b823147h

文献信息

• Observation of acetyl phosphate formation in mammalian mitochondria using real-time in-organelle NMR metabolomics
  作者：Wen Jun Xu、He Wen、Han Sun Kim、Yoon-Joo Ko、Seung-Mo Dong、In-Sun Park、Jong In Yook、Sunghyouk Park

  DOI：10.1073/pnas.1720908115

  日期：2018.4.17

  for the monitoring of mitochondrial metabolic changes in real time. The approach identified acetyl phosphate from human mitochondria, whose production has been largely neglected in eukaryotic metabolism since its first description about 70 years ago in bacteria. The kinetic profile of acetyl phosphate formation was biphasic, and its transient nature suggested its role as a metabolic intermediate. The

  最近的研究指出线粒体代谢改变与癌症之间的联系，对线粒体代谢的详细了解需要实时检测其代谢产物。采用异核2D NMR光谱和13 C 3-丙酮酸盐，我们提出了可以实时监测线粒体代谢变化的细胞内代谢组学。该方法从人线粒体中鉴定出乙酰磷酸酯，自从大约70年前在细菌中首次对其描述以来，其生产在真核代谢中已被大大忽略。乙酰磷酸盐形成的动力学曲线是双相的，其瞬时性质表明其作为代谢中间体的作用。该方法还允许通过监测乙酰辅酶A的形成来估计丙酮酸脱氢酶（PDH）酶的活性，而与竞争性胞质代谢无关。结果证实了著名的肿瘤抑制因子p53对线粒体PDH活性的正调节作用。我们的方法可以轻松地应用于其他细胞器特异性代谢研究。
• Mammalian fatty acid synthase activity from crude tissue lysates tracing 13C-labeled substrates using gas chromatography–mass spectrometry
  作者：Michael C. Rudolph、N. Karl Maluf、Elizabeth A. Wellberg、Chris A. Johnson、Robert C. Murphy、Steve M. Anderson

  DOI：10.1016/j.ab.2012.06.013

  日期：2012.9

  Fatty acid synthase (FASN or FAS, EC 2.3.1.85) is the sole mammalian enzyme to synthesize fatty acids de novo from acetyl- and malonyl-coenzyme A (CoA) esters: This article describes a new method that directly quantifies uniformly labeled C-13(16)-labeled palmitate ([C-13(16)]palmitate) by tracing [C-13(2)]acetyl-CoA and [C-13(3)]malonyl-CoA using an in vitro FASN assay. This method used gas chromatography-mass spectrometry (GC-MS) to detect [C-13(16)]palmitate carboxylate anions (m/z 271) of pentafluorobenzyl (PFB) derivatives and was highly sensitive at femtomole quantities. Uniformly incorporated [C-13(16)]palmitate was the primary product of both recombinant and crude tissue lysate FASN. Quantification of FASN protein within crude tissue lysates ensured equal FASN amounts, preserved steady-state kinetics, and enabled calculation of FASN-specific activity. FASN activity determined by [C-13(16)]palmitate synthesis was consistent with values obtained from p-nicotinamide adenine dinucleotide 2'-phosphate (NADPH) oxidation assays. Analysis of FASN activity from tissue extracts was not hampered by contaminating enzymes or preexisting fatty acids. Crude mammary gland and liver lysates had significantly different activities at 82 and 65 nmol min(-1) mg(-1), respectively, suggesting that tissue-specific activity levels differ in a manner unrelated to FASN amount. GC-MS quantification of [C-13(16)]palmitate synthesis permits sensitive evaluation of FASN activity from tissues of varied physiological states and of purified FASN activity in the presence of modifying proteins, enzymes, or drugs. (C) 2012 Elsevier Inc. All rights reserved.
• Enantioselective desymmetrisation of citric acid catalysed by the substrate-tolerant petrobactin biosynthetic enzyme AsbA
  作者：Daniel Oves-Costales、Lijiang Song、Gregory L. Challis

  DOI：10.1039/b823147h

  日期：——

  AsbA catalyses the highly enantioselective desymmetrisation of citric acid via ATP-dependent condensation with spermidine, as well as the condensation of citric acid with several spermidine analogues and the condensation of the citric acid analogue tricarballylic acid with spermidine, suggesting that it may be a useful biocatalyst for asymmetric synthesis.

  AsbA 通过 ATP 依赖的亚精胺缩合催化柠檬酸的高度对映选择性去对称化，以及柠檬酸与几种亚精胺类似物的缩合以及柠檬酸类似物三羧酸与亚精胺的缩合，表明它可能是一种有用的生物催化剂用于不对称合成。