mono-3'-O-alanyl-AMP | 30759-34-3

• 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: mono-3'-O-alanyl-AMP
• 英文别名: 3'-L-alanyl-AMP；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(phosphonooxymethyl)oxolan-3-yl] (2S)-2-aminopropanoate
• CAS: 30759-34-3
• 化学式: C₁₃H₁₉N₆O₈P
• 分子量: 418.303
• InChiKey: ZUGFBNMTMJLCQZ-MACXSXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  2-Amino-1-benzoimidazol-1-yl-propan-1-one; compound with toluene-4-sulfonic acid 、 5'-腺嘌呤核苷酸 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 mono-3'-O-alanyl-AMP 、 O2'-alanyl-[5']adenylic acid
  参考文献：
  名称：

  Purygin, P. P., Journal of general chemistry of the USSR, 1984, vol. 54, p. 851 - 852

  摘要：

  DOI：

文献信息

• Purygin, P. P., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1713 - 1715
  作者：Purygin, P. P.

  DOI：——

  日期：——
• Structural Basis for the Exceptional Stability of Bisaminoacylated Nucleotides and Transfer RNAs
  作者：Maria Duca、Carl O. Trindle、Sidney M. Hecht

  DOI：10.1021/ja203994e

  日期：2011.7.27

  At least one bisaminoacyl-tRNA is synthesized in nature (by Therm us thermophilus phenylalanyl-tRNA synthetase), and many disubstituted tRNAs have been prepared in vitro. Such misacylated tRNAs are able to participate in protein synthesis, even though they lack the free 2'-OH group of the 3'-terminal adenosine moiety. Their ready participation in protein synthesis implies significant chemical reactivity. The basis for this reactivity has been documented previously. Surprisingly, the aminoacyl moieties of these tRNAs also exhibit exceptional chemical stability. In the present report, bisaminoacylated nucleotides are investigated computationally and experimentally to define the basis for the stability of such species. Molecular modeling of bisalanyl-AMP in the absence of solvent and in the presence of a limited number of water molecules revealed two common features among the low-energy structures. The first was the presence of H-bonding interactions between the two aminoacyl moieties. The second was the presence of a H-bonding interaction between the 2'-O-alanyl moiety and the N-3 atom of the adenine nucleobase, typically mediated through a water molecule. The prediction of an interaction between an aminoacyl moiety and the adenine nudeobase was confirmed experimentally by comparing the behavior of bisalanyl-AMP and bisalanyl-UMP in the presence of model nucleophiles. This study suggests a possible role for the adenosine moiety at the 3'-end of aminoanyl-tRNAs in controlling the stability and reactivity of the aminoacyl moiety and has important implications for the reactivity and stability of normal aminoacyl-tRNAs.
• Purygin, P. P., Journal of general chemistry of the USSR, 1984, vol. 54, p. 851 - 852
  作者：Purygin, P. P.

  DOI：——

  日期：——