N6-Etheno-AMP | 37482-16-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: N6-Etheno-AMP
• 英文别名: 1,N⁶-ethenoadenosine 5'-monophosphate；1,N⁶-ethenoadenosine 5'-phosphate；1,N⁶-etheno-AMP；ε-AMP；1-imidazo[2,1-i]purin-3-yl-O⁵-phosphono-β-D-1-deoxy-ribofuranose；1,N6-Ethenoadenosin-5'-monophosphat；Etheno-adenosine monophosphate；[(2R,3S,4R,5R)-3,4-dihydroxy-5-imidazo[2,1-f]purin-3-yloxolan-2-yl]methyl dihydrogen phosphate
• CAS: 37482-16-9
• 化学式: C₁₂H₁₄N₅O₇P
• 分子量: 371.246
• InChiKey: IRLXSDZTLYOBQH-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N6-Etheno-AMP 在 Meiothermus ruber polyphosphate kinase D₁₂₇S 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 生成 1,N⁶-ethenoadenosine triphosphate 、 [(2R,3S,4R,5R)-3,4-二羟基-5-咪唑并[2,1-f]嘌呤-3-基四氢呋喃-2-基]甲基膦酰磷酸氢酯
  参考文献：
  名称：

  10.1002/cctc.202400181

  摘要：

  AbstractPolyphosphate kinases (PPKs) are valuable biocatalysts for ATP cofactor regeneration as well as for the phosphorylation of non‐canonical nucleotides. The versatility of PPKs in the latter application is defined by their substrate scope. In this study, we investigate the substrate spectrum of the PPK2‐III enzyme from Meiothermus ruber (MrPPK) for the conversion of canonical and non‐canonical (deoxy)‐ribonucleotides. The enzyme shows high substrate promiscuity for purine and to minor degree pyrimidine substrates, with an overall preference for the native substrate AMP. With structure guided rational amino acid exchanges in the active site, we produced an MrPPK variant with improved activity for a broad variety of purine nucleotides. While the preference for AMP is lost, conversion of nucleotides without a 6‐amino function at the purine moiety is increased. This MrPPK variant is a versatile biocatalyst for the synthesis of non‐canonical nucleotides and could also be useful as a GTP cofactor regeneration system.

  DOI：

  10.1002/cctc.202400181
• 作为产物：
  描述：

  氯乙醛 、 5'-腺嘌呤核苷酸 以 aq. phosphate buffer 为溶剂， 反应 0.25h， 生成 N6-Etheno-AMP
  参考文献：
  名称：

  一种新的一锅法荧光衍生化策略，用于高灵敏度的 microRNA 分析。

  摘要：

  MicroRNA （miRNA） 在发育和凋亡过程中调节超过 30% 的哺乳动物基因的表达，miRNA 的异常表达可能导致一系列人类病理。因此，miRNA 分析对于疾病诊断很有价值。在这项工作中，开发了一种新的用于 miRNA 分析的一锅法荧光衍生化策略。使用仪器方法（包括液相色谱、荧光光谱和质谱）探索衍生化反应的机制。在 100 °C 下，核酸中的腺嘌呤与 2-氯乙醛 （CAA） 反应，形成高荧光 N6-乙烯酸腺嘌呤 （ε-腺嘌呤） 并从 miRNA 序列中分离。 这是第一个实验证据，证明形成的 ε-腺嘌呤和水介导的氢键相互作用在 2'-和 3'-位置的氧阴离子之间的相互作用显着稳定了氧代碳苯，这使得 miRNA 的脱嘌呤和衍生化非常有效。基于这种衍生化策略，开发了一种简单灵敏的高效液相色谱法用于 miRNA 的定量测定。HPLC 方法与磁性固相萃取 （MSPE） 相结合，可用于测定血清样品中亚皮摩尔水平的

  DOI：

  10.1002/chem.201905639

文献信息

• Modification of adenine and cytosine derivatives with bromoacetaldehyde.
  作者：KIKUKO KAYASUGA-MIKADO、TERUKO HASHIMOTO、TOMOE NEGISHI、KAZUO NEGISHI、HIKOYA HAYATSU

  DOI：10.1248/cpb.28.932

  日期：——

  Bromoacetaldehyde reacted with adenosine 5'-phosphate and cytidine more rapidly than chloroacetaldehyde to give 1, N6-ethenoadenosine 5'-phosphate and 3, N4-ethenocytidine, respectively. The pH-dependence of the rates of these reactions was similar to that of the chloroacetaldehyde modifications reported in the literature ; i.e. the reactions proceed smoothly in the pH range of 5 to 7. When applied to polynucleotides, bromoacetaldehyde reacted with adenine and cytosine residues located in single-stranded regions but not with those in double-stranded regions. Guanosine 5'-phosphate reacted with bromoacetaldehyde at pH 7 but only very slowly at pH 5. Bromoacetaldehyde may be useful as a more reactive subtitute for chloroacetaldehyde. Bromoacetaldehyde showed little mutagenic activity when assayed on Salmonella typhymurium TA 100.

  溴乙醛与腺苷5'-磷酸和胞苷的反应速率比氯乙醛更快，分别生成1,N6-乙烯基腺苷5'-磷酸和3,N4-乙烯基胞苷。这些反应的pH依赖性与文献中报道的氯乙醛修饰反应相似；即反应在pH 5至7的范围内顺利进行。当应用于多聚核苷酸时，溴乙醛与位于单链区域的腺嘌呤和胞嘧啶残基发生反应，而不与双链区域的这些残基反应。鸟苷5'-磷酸在pH 7时与溴乙醛反应，但在pH 5时仅非常缓慢地反应。溴乙醛可能作为氯乙醛的一个更具反应活性的替代品。在检测于鼠伤寒沙门氏菌TA 100时，溴乙醛显示出很低的诱变活性。
• Methods for modulating taste receptors
  申请人：MARS, INCORPORATED

  公开号：US11185100B2

  公开（公告）日：2021-11-30

  Amino acids present in domains of an umami taste receptor are described herein, wherein the amino acids interact with at least one nucleotide derivative and/or at least one transmembrane compound that potentiates, modulates, increases, and/or enhances the activity of the umami receptor. Such compounds can be used in flavor compositions to enhance the umami taste and/or palatability of food products.

  本文描述了存在于鲜味受体结构域中的氨基酸，其中氨基酸与至少一种核苷酸衍生物和/或至少一种跨膜化合物相互作用，从而增强、调节、增加和/或提高鲜味受体的活性。此类化合物可用于调味组合物，以增强食品的鲜味和/或适口性。
• Synthesis of 2-Azido-1,N⁶-Etheno and 2-Azido Analogs of Deoxyadenosine as Nucleotide Photoaffinity Probes
  作者：Diane Flaherty、Preeti Balse、Ke Li、Bob M. Moore、Michael B. Doughty

  DOI：10.1080/15257779508014653

  日期：1995.2
• FLAVOR COMPOSITIONS AND PET FOOD PRODUCTS CONTAINING THE SAME
  申请人：MARS, INCORPORATED

  公开号：US20180168208A1

  公开（公告）日：2018-06-21

  A flavor composition comprising at least one nucleotide derivative and/or at least one transmembrane compound that modulates, increases and/or enhances the activity of an umami receptor is provided that can be used to enhance the umami taste and/or palatability of food products. In certain, non-limiting embodiments, the flavor composition comprises at least one nucleotide derivative and/or at least one transmembrane compound, optionally at least one nucleotide, optionally at least one first amino acid, optionally at least one second amino acid.
• METHODS FOR MODULATING TASTE RECEPTORS
  申请人：MARS, INCORPORATED

  公开号：US20180255813A1

  公开（公告）日：2018-09-13

  Amino acids present in domains of an umami taste receptor are described herein, wherein the amino acids interact with at least one nucleotide derivative and/or at least one transmembrane compound that potentiates, modulates, increases, and/or enhances the activity of the umami receptor. Such compounds can be used in flavor compositions to enhance the umami taste and/or palatability of food products.