<6-3H>glucose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <6-3H>glucose
• 英文别名: [6-³H]D-glucose；(3R,4S,5S,6R)-6-[hydroxy(tritio)methyl]oxane-2,3,4,5-tetrol
• 化学式: C₆H₁₂O₆
• 分子量: 182.15
• InChiKey: WQZGKKKJIJFFOK-RGUNKWSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <6-3H>glucose 在 DL-谷氨酰胺 作用下， 生成
  参考文献：
  名称：

  Enzymic Synthesis of NAD+ with the Specific Incorporation of Atomic Labels

  摘要：

  An enzymatic synthesis is described for the production of NAD(+) labeled with a radioactive or stable isotope at any desired position in the AMP or NMN(+) portions of the molecule. In the first step, ten enzyme-catalyzed reactions are coupled for the synthesis of nicotinic acid adenine dinucleotide (NaAD(+)) from glucose, nicotinic acid, and ATP. NAD(+) is formed from NaAD(+) and glutamine in the second step. Oxidized nicotinamide adenine dinucleotide was synthesized with H-3, C-14, or N-15 label specifically incorporated in the ribose or nicotinamide of the NMN(+) portion of NAD(+) as [H(N)1'H-3]NAD(+), [H(N)2'-H-3]NAD(+), [H(N)4'-H-3]NAD(+), [H(N)5'-H-3]NAD(+), [C(N)1'-C-14]NAD(+), [C(N)5'-C-14]NAD(+), [N(N)1-N-15, C(N)1'-C-14]NAD(+), and [N(N)1-N-15, C(N)5'-C-14]NAD(+). Nuclear magnetic resonance spectroscopy of [H(N)2'-H-2]NAD(+) as well as enzymatic degradation were used to verify the position of labels. Appropriately labeled glucose, ribose 5-phosphate, or nicotinic acid were the starting materials and were converted to NAD(+) using enzymes from the pentose pathway and the pathway for NAD(+) de novo synthesis. Yields of purified NAD(+) to 96% were obtained from starting glucose. The labeled NAD(+) is catalytically competent and is chromatographically and spectrophotometrically indistinguishable from authentic NAD(+). By using specifically labeled ATP as a precursor (Parkin, D. W.; Schramm, V. L. Biochemistry 1987, 26, 913-920), the method is readily adaptable for the synthesis of NAD(+) with single or multiple atomic labels at various positions in the AMP portion of the molecule. NAD(+) was synthesized from [8-C-14]ATP to give [C(A)8-C-14]NAD(+) as an example. Together these methods provide a general scheme for the efficient synthesis of NAD(+) of high purity with H-3, C-14, Or Other labels at any nonexchangeable position of the NMN(+) or AMP portions of the NAD(+) molecule.

  DOI：

  10.1021/ja00094a006

文献信息

• Recycling Nicotinamide. The Transition-State Structure of Human Nicotinamide Phosphoribosyltransferase
  作者：Emmanuel S. Burgos、Mathew J. Vetticatt、Vern L. Schramm

  DOI：10.1021/ja310180c

  日期：2013.3.6

  determined the TS structure for pyrophosphorolysis of nicotinamide mononucleotide (NMN) from kinetic isotope effects (KIEs). With the natural substrates, NMN and pyrophosphate (PPi), the intrinsic KIEs of [1'-(14)C], [1-(15)N], [1'-(3)H], and [2'-(3)H] are 1.047, 1.029, 1.154, and 1.093, respectively. A unique quantum computational approach was used for TS analysis that included structural elements of the catalytic

  人烟酰胺磷酸核糖转移酶 (NAMPT) 补充 NAD 库并控制去乙酰化酶、单和聚 (ADP-核糖) 聚合酶以及 NAD 核苷酶的活性。酶过渡态 (TS) 的性质对于理解 NAMPT 的功能至关重要。我们通过动力学同位素效应 (KIE) 确定了烟酰胺单核苷酸 (NMN) 焦磷酸解的 TS 结构。使用天然底物 NMN 和焦磷酸盐 (PPi)，内在 KIE 为 [1'-(14)C]、[1-(15)N]、[1'-(3)H] 和 [2'- (3)H]分别为1.047、1.029、1.154和1.093。使用独特的量子计算方法进行 TS 分析，其中包括催化位点的结构元素。在没有约束（例如施加扭转角）的情况下，理论数据和实验数据非常一致。量子力学计算纳入了一个关键的催化位点残基（D313）、两个镁原子和配位水分子。 TS 模型预测初级 (14)C、α-次级 (3)H、β-次级 (3)H 和初级 (15)N
• METHOD FOR ANALYSING METABOLITES
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP1695088A1

  公开（公告）日：2006-08-30
• [EN] METHOD FOR ANALYSING METABOLITES<br/>[FR] PROCEDE D'ANALYSE DE METABOLITES
  申请人：MAX PLANCK GESELLLSCHAFT ZUR F

  公开号：WO2005059556A1

  公开（公告）日：2005-06-30

  Described is a method for analysing the metabolites of a biological sample which comprises quantitatively determining one or more metabolites in said sample in a way that said quantitative determination resolves isotopic mass differences within one metabolite, said method being characterized in that the sample comprises or is derived from a cell which has been maintained under conditions allowing the uptake of an isotopically labeled metabolizable compound so that the metabolites in said cell are saturated with the isotope with which said metabolizable compound is labeled. This method may further comprise, prior to quantitative determining the metabolites, combining the biological sample (i.e. the first biological sample) with a second biological sample in which the metabolites are not isotopically labeled or are isotopically labeled differently from the first biological sample; and determining in said biological samples the relative quantity of metabolites which differ by their isotopical label. Furthermore described is a set of isotopically labeled metabolites obtainable by applying this method, as well as kits facilitating the application of this method and corresponding uses.
• Enzymic Synthesis of NAD+ with the Specific Incorporation of Atomic Labels
  作者：Kathleen A. Rising、Vern L. Schramm

  DOI：10.1021/ja00094a006

  日期：1994.7

  An enzymatic synthesis is described for the production of NAD(+) labeled with a radioactive or stable isotope at any desired position in the AMP or NMN(+) portions of the molecule. In the first step, ten enzyme-catalyzed reactions are coupled for the synthesis of nicotinic acid adenine dinucleotide (NaAD(+)) from glucose, nicotinic acid, and ATP. NAD(+) is formed from NaAD(+) and glutamine in the second step. Oxidized nicotinamide adenine dinucleotide was synthesized with H-3, C-14, or N-15 label specifically incorporated in the ribose or nicotinamide of the NMN(+) portion of NAD(+) as [H(N)1'H-3]NAD(+), [H(N)2'-H-3]NAD(+), [H(N)4'-H-3]NAD(+), [H(N)5'-H-3]NAD(+), [C(N)1'-C-14]NAD(+), [C(N)5'-C-14]NAD(+), [N(N)1-N-15, C(N)1'-C-14]NAD(+), and [N(N)1-N-15, C(N)5'-C-14]NAD(+). Nuclear magnetic resonance spectroscopy of [H(N)2'-H-2]NAD(+) as well as enzymatic degradation were used to verify the position of labels. Appropriately labeled glucose, ribose 5-phosphate, or nicotinic acid were the starting materials and were converted to NAD(+) using enzymes from the pentose pathway and the pathway for NAD(+) de novo synthesis. Yields of purified NAD(+) to 96% were obtained from starting glucose. The labeled NAD(+) is catalytically competent and is chromatographically and spectrophotometrically indistinguishable from authentic NAD(+). By using specifically labeled ATP as a precursor (Parkin, D. W.; Schramm, V. L. Biochemistry 1987, 26, 913-920), the method is readily adaptable for the synthesis of NAD(+) with single or multiple atomic labels at various positions in the AMP portion of the molecule. NAD(+) was synthesized from [8-C-14]ATP to give [C(A)8-C-14]NAD(+) as an example. Together these methods provide a general scheme for the efficient synthesis of NAD(+) of high purity with H-3, C-14, Or Other labels at any nonexchangeable position of the NMN(+) or AMP portions of the NAD(+) molecule.