乙酰基腺苷酸 | 13015-87-7

• 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: 乙酰基腺苷酸
• 英文名称: adenosine-5'-phosphoric acetic anhydride
• 英文别名: acetyl adenylate；acetic [5']adenylic anhydride；[5']adenylic acid acetic acid-anhydride；[5']Adenylsaeure-essigsaeure-anhydrid；Acetyladenylat；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] acetate
• CAS: 13015-87-7
• 化学式: C₁₂H₁₆N₅O₈P
• 分子量: 389.261
• InChiKey: UBPVOHPZRZIJHM-WOUKDFQISA-N

物化性质

• 沸点：
  739.3±70.0 °C(Predicted)
• 密度：
  2.07±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  192
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙酰基腺苷酸 在 咪唑 、 水 作用下， 生成 O^3'-acetyl-[5']adenylic acid 、 O^2'-acetyl-[5']adenylic acid
  参考文献：
  名称：

  酰基腺苷酸和咪唑的非酶促反应。

  摘要：

  DOI：

  10.1016/0006-3002(57)90185-3
• 作为产物：
  描述：

  sodium acetate 、 5’-三磷酸腺苷 在 acetyl-coa-synthetase 、 magnesium chloride 作用下， 生成 乙酰基腺苷酸
  参考文献：
  名称：

  Webster; Campagnari, Journal of Biological Chemistry, 1962, vol. 237, p. 1050,1051

  摘要：

  DOI：

文献信息

• Acetate-dependent tRNA acetylation required for decoding fidelity in protein synthesis
  作者：Takaaki Taniguchi、Kenjyo Miyauchi、Yuriko Sakaguchi、Seisuke Yamashita、Akiko Soma、Kozo Tomita、Tsutomu Suzuki

  DOI：10.1038/s41589-018-0119-z

  日期：2018.11

  Modification of tRNA anticodons plays a critical role in ensuring accurate translation. N4-acetylcytidine (ac4C) is present at the anticodon first position (position 34) of bacterial elongator tRNAMet. Herein, we identified Bacillus subtilis ylbM (renamed tmcAL) as a novel gene responsible for ac4C34 formation. Unlike general acetyltransferases that use acetyl-CoA, TmcAL activates an acetate ion to form acetyladenylate and then catalyzes ac4C34 formation through a mechanism similar to tRNA aminoacylation. The crystal structure of TmcAL with an ATP analog reveals the molecular basis of ac4C34 formation. The ΔtmcAL strain displayed a cold-sensitive phenotype and a strong genetic interaction with tilS that encodes the enzyme responsible for synthesizing lysidine (L) at position 34 of tRNAIle to facilitate AUA decoding. Mistranslation of the AUA codon as Met in the ΔtmcAL strain upon tilS repression suggests that ac4C34 modification of tRNAMet and L34 modification of tRNAIle act cooperatively to prevent misdecoding of the AUA codon. A comparative genomic approach identified a novel acetate-dependent tRNA-modifying enzyme that catalyzes RNA acetylation with a mechanism similar to tRNA aminoacylation. This modification maintains decoding fidelity in protein synthesis.

  tRNA反密码子的修饰在确保准确翻译方面起着关键作用。N4-乙酰胞苷（ac4C）存在于细菌延长子tRNAMet的反密码子第一位置（第34位）。在此，我们鉴定出枯草芽孢杆菌ylbM（重命名为tmcAL）是负责形成ac4C34的新基因。与使用乙酰辅酶A的一般乙酰转移酶不同，TmcAL激活乙酸离子形成乙酰腺苷酸，然后通过类似于tRNA氨基酰化的机制催化ac4C34的形成。TmcAL与ATP类似物的晶体结构揭示了ac4C34形成的分子基础。dtmcAL菌株表现出对冷敏感的表型，并与tilS存在强烈的遗传相互作用，tilS编码负责在tRNAIle的第34位合成赖氨酸（L）的酶，以促进AUA
• Kellerman, Journal of Biological Chemistry, 1958, vol. 231, p. 427,433-435
  作者：Kellerman

  DOI：——

  日期：——
• Berg, Journal of Biological Chemistry, 1956, vol. 222, p. 1015,1017
  作者：Berg

  DOI：——

  日期：——
• Characterization of Acyl Adenyl Anhydrides:  Differences in the Hydrolytic Rates of Fatty Acyl-AMP and Aminoacyl-AMP Derivatives
  作者：Otto F. Schall、Iwao Suzuki、Clare L. Murray、Jeffrey I. Gordon、George W. Gokel

  DOI：10.1021/jo971874f

  日期：1998.11.1

  An improved procedure has been developed to prepare RCOOPO2-Ado (R = C6H13 and C15H31), the intermediate in the enzymatic synthesis of acyl-CoA's. The product has been characterized by spectral methods which, in turn, were used to define the hydrolysis rates of RCO-AMP. When R is a fatty acyl group, the hydrolysis rate is 10-fold slower than when R is aminoacyl. In both cases, the hydrolysis rate is enhanced by Mg2+. We speculate that the rate acceleration is due to intramolecular participation of the second carbonyl group in the aminoacyl residue.
• Whitehouse et al., Journal of Biological Chemistry, 1957, vol. 226, p. 813,814
  作者：Whitehouse et al.

  DOI：——

  日期：——