nicotinamide adenine dinucleotide | 58-68-4

• 物质功能分类: 生物化工 - 酶及辅酶类
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （5'->5'）-二核苷酸
• 英文名称: nicotinamide adenine dinucleotide
• 英文别名: NADH；β-NADH；beta-Nicotinamide adenine dinucleotide, reduced；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 58-68-4
• 化学式: C₂₁H₂₉N₇O₁₄P₂
• 分子量: 665.447
• InChiKey: BOPGDPNILDQYTO-DQQFMEOOSA-N

物化性质

• 沸点：
  1081.8±75.0 °C(Predicted)
• 密度：
  2.18±0.1 g/cm3(Predicted)
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  318
• 氢给体数：
  8
• 氢受体数：
  19

制备方法与用途

应用领域中的辅酶NADH是一种还原型烟酰胺腺嘌呤二核苷酸，它在许多生物体内的化学反应中充当递氢体的角色。辅酶NADH对于多种氧化还原反应至关重要，如呼吸作用和光合作用等过程。

反应信息

• 作为反应物：
  描述：

  nicotinamide adenine dinucleotide 在 对苯醌 作用下， 以 水 、 乙腈 为溶剂， 生成 NAD
  参考文献：
  名称：

  Mechanism of the oxidation of NADH by quinones. Energetics of one-electron and hydride routes

  摘要：

  DOI：

  10.1021/ja00288a035
• 作为产物：
  描述：

  NAD 在 苹果酸 sodium hydroxide 、 聚甘氨酸 作用下， 以 水 为溶剂， 生成 nicotinamide adenine dinucleotide
  参考文献：
  名称：

  Purification, Characterization, and Overexpression of Psychrophilic and Thermolabile Malate Dehydrogenase of a Novel Antarctic Psychrotolerant,Flavobacterium frigidimarisKUC-1

  摘要：

  我们从南极海水中分离出的一种新型心理耐受性黄杆菌（Flavobacterium frigidimaris KUC-1）中纯化出了具有心理亲和性和热稳定性的苹果酸脱氢酶。该酶是一种同源四聚体，分子量约为 123 k，亚基分子量约为 32 k。该酶需要 NAD(P)+ 作为辅酶，专门催化 L-苹果酸的氧化和草酰乙酸的还原。反应通过有序的双生物机制进行。该酶极易受热处理影响，在 40 °C 时的半衰期估计为 3.0 分钟。30 °C时，L-苹果酸和NAD+的kcat/Km（μM-1-s-1）值分别为289和2,790。该酶对辅酶烟酰胺分子 C4 位的氢转移具有亲 R 立体特异性。该酶含有 311 个氨基酸残基，脯氨酸和精氨酸残基的数量远低于其他苹果酸脱氢酶。

  DOI：

  10.1271/bbb.69.2146
• 作为试剂：
  描述：

  甲基苯醌 在 diaphorase from Clostridium kluyveri 、 nicotinamide adenine dinucleotide 作用下， 以 aq. phosphate buffer 为溶剂， 生成 甲基氢醌
  参考文献：
  名称：

  酶激活的化学发光铁载体二氧杂环丁烷探针能够选择性且高灵敏度地检测细菌病原体

  摘要：

  敏感的诊断对于成功治疗细菌感染至关重要。细菌特异性、增强吸收的铁载体载体与酶诱导化学发光二氧杂环丁烷的结合使得能够对“ESKAPE”病原体进行广谱检测。该探针在人血浆中表现出高灵敏度，还可以检测细胞内的革兰氏阳性和阴性细菌。

  DOI：

  10.1002/anie.202201423

文献信息

• First Estimation of C₄−H Bond Dissociation Energies of NADH and Its Radical Cation in Aqueous Solution
  作者：Xiao-Qing Zhu、Yuan Yang、Ming Zhang、Jin-Pei Cheng

  DOI：10.1021/ja0385179

  日期：2003.12.1

  and homolytic C4-H bond dissociation energies of NADH and its radical cation (NADH*+) in aqueous solution were estimated according to the reaction of NADH with N,N,N',N'-tetramethyl-p-phenylenediamine radical cation perchlorate (TMPA*+) in aqueous solution. The results show that the values of the heterolytic and homolytic C4-H bond dissociation energies of NADH in aqueous solution are 53.6 and 79.3

  根据NADH与N,N,N',N'-四甲基-对苯二胺自由基阳离子的反应，估算了NADH及其自由基阳离子(NADH*+)在水溶液中的异裂和均裂C4-H键解离能高氯酸盐 (TMPA*+) 水溶液。结果表明，NADH在水溶液中的异裂和均裂C4-H键解离能分别为53.6和79.3 kcal/mol；NADH*+*+ 在水溶液中的异裂和均裂 C4-H 键解离能值分别为 5.1 和 36.3 kcal/mol，据我们所知，这是首次报道。应该相信，本工作中公开的这种能量信息为理解体内辅酶对 NADH/NAD+ 的氧化还原相互转化的机制提供了线索。
• Deuterium isotope effects for the nonenzymic and glutamate dehydrogenase catalyzed reduction of an .alpha.-imino acid by NADH
  作者：R. Srinivasan、Harvey F. Fisher

  DOI：10.1021/ja00300a038

  日期：1985.7
• Efficient Catalytic Interconversion between NADH and NAD⁺ Accompanied by Generation and Consumption of Hydrogen with a Water-Soluble Iridium Complex at Ambient Pressure and Temperature
  作者：Yuta Maenaka、Tomoyoshi Suenobu、Shunichi Fukuzumi

  DOI：10.1021/ja207785f

  日期：2012.1.11

  Regioselective hydrogenation of the oxidized form of beta-nicotinamide adenine dinucleotide (NAD(+)) to the reduced form (NADH) with hydrogen (H-2) has successfully been achieved in the presence of a catalytic amount of a [C,N] cyclometalated organoiridium complex [Ir-III(Cp*)(4-(1H-pyrazol-1-yl-kappa N-2)benzoic acid-kappa C-3)(H2O)](2) SO4 [1](2)center dot SO4 under an atmospheric pressure of H-2 at room temperature in weakly basic water. The structure of the corresponding benzoate complex Ir-III(Cp*)(4-(1H-pyrazol-1-yl-kappa N-2)-benzoate-kappa C-3)(H2O) 2 has been revealed by X-ray single-crystal structure analysis. The corresponding iridium hydride complex formed under an atmospheric pressure of H-2 undergoes the 1,4-selective hydrogenation of NAD(+) to form 1,4-NADH. On the other hand, in weakly acidic water the complex 1 was found to catalyze the hydrogen evolution from NADH to produce NAD(+) without photoirradiation at room temperature. NAD(+) exhibited an inhibitory behavior in both catalytic hydrogenation of NAD(+) with H-2 and H-2 evolution from NADH due to the binding of NAD(+) to the catalyst. The overall catalytic mechanism of interconversion between NADH and NAD(+) accompanied by generation and consumption of H-2 was revealed on the basis of the kinetic analysis and detection of the catalytic intermediates.
• Horiuchi, Tatsuo; Kurokawa, Toshiko, Agricultural and Biological Chemistry, 1989, vol. 53, # 7, p. 1919 - 1926
  作者：Horiuchi, Tatsuo、Kurokawa, Toshiko

  DOI：——

  日期：——
• Factors influencing the operational stability of NADPH-dependent alcohol dehydrogenase and an NADH-dependent variant thereof in gas/solid reactors
  作者：Liliya Kulishova、Kerasina Dimoula、Max Jordan、Astrid Wirtz、Diana Hofmann、Beatrix Santiago-Schübel、Jörg Fitter、Martina Pohl、Antje C. Spiess

  DOI：10.1016/j.molcatb.2010.09.005

  日期：2010.12

  The continuous enzymatic gas/solid bio-reactor serves both for the production of volatile fine chemicals and flavors on an industrial scale and for thermodynamically controlled investigation of substrate and water effects on enzyme preparations for research purposes. Here, we comparatively investigated the molecular effects on the operational stability of NADPH-dependent Lactobacillus brevis alcohol dehydrogenase and an NADH-dependent variant thereof, LbADH G37D, in the gas/solid bioreactor. The reference reaction is the reduction of acetophenone to (R)-1-phenylethanol with concomitant oxidation of 2-propanol to acetone for the purpose of regeneration of the redox cofactor.It could be clearly shown that not the thermostability of the cofactor, but the thermostability of the proteins in the solid dry state govern the order of magnitude of the operational stability of both purified enzymes in the gas/solid reactor at low thermodynamic activity of water and substrate. However, at higher thermodynamic activity the operational stability in the gas/solid reactor is overlaid by stabilizing and destabilizing effects of the substrates that require further investigation. We demonstrated first evidence that the substrate affinity of the two variants in the gas/solid reactor is similar to the affinity in aqueous medium. We could also show that partial unfolding of the proteins with subsequent aggregation are the factors governing protein thermo-in-stability both in the dissolved and in the dry state. Thus. stability investigations of enzymes in the dry state are suggested to predict their basal level of operational stability in gas/solid reactions. (C) 2010 Elsevier B.V. All rights reserved.