烟酰胺1,N(6)-乙烯桥腺嘌呤二核苷酸

• 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
• 中文名称: 烟酰胺1,N(6)-乙烯桥腺嘌呤二核苷酸
• 英文名称: 1,N6-ethenonicotinamide adenine dinucleotide
• 英文别名: nicotinamide 1,N6-ethenoadenine dinucleotide；1,N⁶-etheno-NAD⁺；1,N⁶-etheno NAD⁺；1,N⁶-etheno-NAD；etheno-NAD⁺；e-NAD⁺；[[(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] [(2R,3S,4R,5R)-3,4-dihydroxy-5-(1H-imidazo[2,1-f]purin-3-ium-3-yl)oxolan-2-yl]methyl phosphate
• 化学式: C₂₃H₂₇N₇O₁₄P₂
• 分子量: 687.453
• InChiKey: JCDBQDNBEQHDHK-BSLNIGMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  300
• 氢给体数：
  6
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  烟酰胺1,N(6)-乙烯桥腺嘌呤二核苷酸 在 三乙胺 、 sodium bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以6%的产率得到
  参考文献：
  名称：

  Novel analogs of cyclic-ADP-ribose: 9-Cyclic etheno-ADP-ribose and cyclic etheno-CDP-ribose

  摘要：

  Two novel analogs of cyclic ADP-ribose (cADPR), 9-cyclic etheno-ADP-ribose (1) and cyclic etheno-CDP-ribose (2) were synthesized. We have shown for the first time that enzymatic and biomimetic methods may proceed by different reaction pathways. 1,N-6-Etheno-nicotinamide-adenine dinucleotide (3) was converted into 1 using the biomimetic procedure, whereas ADP-ribosyl cyclase transformed 3 into 4. The unique fluorescence property and the strong Ca2+ mobilizing activity of 1 provide investigators with a useful probe for the study of cADPR-binding proteins. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00428-3

文献信息

• The Preparation of Butyrylated NAD⁺Type of Biological Molecules
  作者：Ki-Jun Hwang、Beom-Tae Kim、Uh-Hyun Kim

  DOI：10.1081/scc-120022168

  日期：2003.1.8

  Butyrylated NAD(+) and its fluorescent analog, 1,N-6-etheno NAD(+) are prepared in good yields by employing two-phase system, i.e., water and CH2Cl2 containing dimethyaminopyridine and excess butyric anhydride. The reaction condition for this reaction is so specific that several other acylating conditions attempted were totally failed, and this developed methodology will be conveniently utilized for the further study of cyclic ADP-ribose (cADPR).
• Novel analogs of cyclic-ADP-ribose: 9-Cyclic etheno-ADP-ribose and cyclic etheno-CDP-ribose
  作者：Fang-Jie Zhang、Charles J. Sih

  DOI：10.1016/0960-894x(96)00428-3

  日期：1996.10

  Two novel analogs of cyclic ADP-ribose (cADPR), 9-cyclic etheno-ADP-ribose (1) and cyclic etheno-CDP-ribose (2) were synthesized. We have shown for the first time that enzymatic and biomimetic methods may proceed by different reaction pathways. 1,N-6-Etheno-nicotinamide-adenine dinucleotide (3) was converted into 1 using the biomimetic procedure, whereas ADP-ribosyl cyclase transformed 3 into 4. The unique fluorescence property and the strong Ca2+ mobilizing activity of 1 provide investigators with a useful probe for the study of cADPR-binding proteins. Copyright (C) 1996 Elsevier Science Ltd