烟酰胺[羰基-14C] | 10119-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 烟酰胺[羰基-14C]
• 英文名称: [carbonyl-¹⁴C]-nicotinamide
• 英文别名: [14C]-nicotinamide；Nicotinamid-(14C)；(Carbonyl-14C)nicotinamide；pyridine-3-carboxamide
• CAS: 10119-18-3
• 化学式: C₆H₆N₂O
• 分子量: 124.115
• InChiKey: DFPAKSUCGFBDDF-ZQBYOMGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 危险品运输编号：
  UN 2910 7

反应信息

• 作为反应物：
  描述：

  β-烟酰胺腺嘌呤二核苷酸 、 烟酰胺[羰基-14C] 在 ADP-ribosylcyclase 、 磷酸二脂酶 、 alkaline phosphatase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  化学酶法合成同位素标记的烟酰胺核糖†

  摘要：

  作为许多反应的辅助因子，NAD +被广泛分散在许多细胞代谢图中。仅此核心氧化还原作用就使NAD +的生物合成备受关注。最近的研究表明，NAD +作为调节广泛关键细胞任务的多种酶的底物，具有新的生物学作用。这些消耗NAD +的酶进一步突出了理解NAD +生物合成途径的重要性。在这项研究中，我们开发了同位素标记的NAD +前体烟酰胺核糖（NR）的化学酶法合成方法。NR异位异构体的合成使我们能够明确确定NR是否有效转化为NAD +在细胞环境中不依赖于烟酰胺的降解，并且以完整形式掺入NAD +中。通用的合成方法以及同位素标记的NR将为进一步破译重要而又复杂的NAD +代谢提供强大的工具。

  DOI：

  10.1039/c8ob00552d

文献信息

• Synthesis of radiolabeled nicotinamide cofactors from labeled pyridines: Versatile probes for enzyme kinetics
  作者：Arundhuti Sen、Vanja Stojković、Amnon Kohen

  DOI：10.1016/j.ab.2012.08.012

  日期：2012.11

  C-14-labeled nicotinamide cofactors are widely employed in biomedical investigations: for example, to delineate C-14-labeled nicotinamide cofactors are widely employed in biomedical investigations, for example, to delineate metabolic pathways, to elucidate enzymatic mechanisms, and as substrates in kinetic isotope effect (KIE) experiments. The C-14 label has generally been located remote from the reactive position, frequently at the adenine ring. Rising costs of commercial precursors and disruptions in the availability of enzymes required for established syntheses have recently made the preparation of labeled nicotinamides such as [Ad-C-14]NADPH unviable. Here, we report the syntheses and characterization of several alternatives: [carbonyl-C-14]NADPH, 4R-[carbonyl-C-14, 4-H-2]NADPH, and [carbonyl-C-14, 4-H-2(2)]NADPH. The new procedures use [carbonyl-C-14]nicotinamide as starting material, because it is significantly cheaper than other commercial C-14 precursors of NADPH, and require only one commercially available enzyme to prepare NAD(P)(+) and NAD(P)H. The proximity of carbonyl-C-14 to the reactive center raises the risk of an inopportune C-14 isotope effect. This concern has been alleviated via competitive KIE measurements with Escherichia coli dihydrofolate reductase (EcDHFR) that use this specific carbonyl-C-14 NADPH. A combination of binding isotope effect and KIE measurements yielded no significant C-12/C-14 isotope effect at the amide carbonyl (KIE = 1.003 +/- 0.004). The reported procedure provides a high-yield, high-purity, and cost-effective alternative to labeled nicotinamide cofactors synthesized by previously published routes. (C) 2012 Elsevier Inc. All rights reserved.