[[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰](2S)-2-氨基-3-苯丙酸酯 | 35874-27-2

• 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
• 中文名称: [[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰](2S)-2-氨基-3-苯丙酸酯
• 英文名称: phenylalaninyl adenylate
• 英文别名: Phe-O-AMP；[5']adenylic acid L-phenylalanine anhydride；[5']Adenylsaeure-L-phenylalanin-anhydrid；Adenosine-5'-[phenylalaninyl-phosphate]；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] (2S)-2-amino-3-phenylpropanoate
• CAS: 35874-27-2
• 化学式: C₁₉H₂₃N₆O₈P
• 分子量: 494.401
• InChiKey: ZFNOOEXYTZPIQS-URQYDQELSA-N

物化性质

• 沸点：
  821.4±75.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  218
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  [5']adenylic acid-(N-benzyloxycarbonyl-L-phenylalanine)-anhydride 在 钯 、 溶剂黄146 作用下， 生成 [[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰](2S)-2-氨基-3-苯丙酸酯
  参考文献：
  名称：

  Moldave et al., Journal of Biological Chemistry, 1959, vol. 234, p. 841,843

  摘要：

  DOI：

文献信息

• Amino Acid Dependent Formation of Phosphate Anhydrides in Water Mediated by Carbonyl Sulfide
  作者：Luke J. Leman、Leslie E. Orgel、M. Reza Ghadiri

  DOI：10.1021/ja056036e

  日期：2006.1.1

  an efficient condensing agent in the context of phosphate chemistry in aqueous solutions. We report that high-energy aminoacyl-phosphate anhydrides and aminoacyl adenylates are generated in solutions containing amino acids, COS, and the corresponding phosphate molecule. We further show that the mixed anhydrides of amino acids and inorganic phosphate are phosphorylating agents, producing pyrophosphate

  硫化羰 (COS) 是火山气体排放和星际气体云的组成部分，在水溶液中的磷酸盐化学背景下被证明是一种有效的冷凝剂。我们报告说，在含有氨基酸、COS 和相应的磷酸盐分子的溶液中会产生高能氨酰磷酸酐和氨酰腺苷酸。我们进一步表明，氨基酸和无机磷酸盐的混合酸酐是磷酸化剂，在 Ca2+ 沉淀存在的情况下，焦磷酸盐的产率高于 30%。这里报道的磷酸的氨基酸依赖性激活与肽的产生同时发生，表明这两个反应可能在益生元地球上共享一个共同的中间体。
• Moriguchi, Tomohisa; Yanagi, Terukazu; Wada, Takeshi, Journal of the Chemical Society. Perkin transactions I, 1999, # 13, p. 1859 - 1865
  作者：Moriguchi, Tomohisa、Yanagi, Terukazu、Wada, Takeshi、Sekine, Mitsuo

  DOI：——

  日期：——
• Adenylation Enzyme Characterization Using γ -18O4-ATP Pyrophosphate Exchange
  作者：Vanessa V. Phelan、Yu Du、John A. McLean、Brian O. Bachmann

  DOI：10.1016/j.chembiol.2009.04.007

  日期：2009.5

  We present here a rapid, highly sensitive nonradioactive assay for adenylation enzyme selectivity determination and characterization. This method measures the isotopic back exchange of unlabeled pyrophosphate into gamma-O-18(4)-labeled ATP via matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MS), electrospray ionization liquid chromatography MS, or electrospray ionization liquid chromatography-tandem MS and is demonstrated for both nonribosomal (TycA, ValA) and ribosomal synthetases (TrpRS, LysRS) of known specificity. This low-volume (6 mu l) method detects as little as 0.01% (600 fmol) exchange, comparable in sensitivity to previously reported radioactive assays and readily adaptable to kinetics measurements and high throughput analysis of a wide spectrum of synthetases. Finally, a previously uncharacterized A-T didomain from anthramycin biosynthesis in the thermophile S. refuinius was demonstrated to selectively activate 4-methyl-3-hydroxyanthranilic acid at 47 degrees C, providing biochemical evidence for a new aromatic beta-amino acid activating adenylation domain and the first functional analysis of the anthramycin biosynthetic gene cluster.
• Berg, Journal of Biological Chemistry, 1958, vol. 233, p. 608
  作者：Berg

  DOI：——

  日期：——
• CATALYTIC RNAs WITH AMINOACYLATION ACTIVITY
  申请人：The Research Foundation of State University of New York

  公开号：EP1232285B1

  公开（公告）日：2008-06-04