monomethyl adenosine 2'-monophosphate | 74494-54-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: monomethyl adenosine 2'-monophosphate
• 英文别名: [2']adenylic acid monomethyl ester；[2']Adenylsaeure-monomethylester；[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] methyl hydrogen phosphate
• CAS: 74494-54-5
• 化学式: C₁₁H₁₆N₅O₇P
• 分子量: 361.251
• InChiKey: IOGSTFJBOOHNTQ-IOSLPCCCSA-N

物化性质

• 沸点：
  721.8±70.0 °C(Predicted)
• 密度：
  2.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  175
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  monomethyl adenosine 2'-monophosphate 生成 腺嘌呤
  参考文献：
  名称：

  OIVANEN, MIKKO;SCHNELL, RALF;PFLEIDERER, WOLFRANG;LONNBERG, HARRI, J. ORG. CHEM., 56,(1991) N1, C. 3623-3628

  摘要：

  DOI：
• 作为产物：
  描述：

  monomethyl adenosine 3'-monophosphate 生成 monomethyl adenosine 2'-monophosphate
  参考文献：
  名称：

  OIVANEN, MIKKO;SCHNELL, RALF;PFLEIDERER, WOLFRANG;LONNBERG, HARRI, J. ORG. CHEM., 56,(1991) N1, C. 3623-3628

  摘要：

  DOI：

文献信息

• Barker et al., Journal of the Chemical Society, 1957, p. 3786,3788, 3791
  作者：Barker et al.

  DOI：——

  日期：——
• Heppel; Whitfeld, Biochemical Journal, 1955, vol. 60, p. 1,2
  作者：Heppel、Whitfeld

  DOI：——

  日期：——
• Interconversion and hydrolysis of monomethyl and monoisopropyl esters of adenosine 2'- and 3'-monophosphates: kinetics and mechanisms
  作者：Mikko Oivanen、Ralf Schnell、Wolfgang Pfleiderer、Harri Lonnberg

  DOI：10.1021/jo00011a032

  日期：1991.5

  First-order rate constants for mutual isomerization and hydrolytic cleavage of the monomethyl and monoisopropyl esters of adenosine 2'- and 3'-monophosphates (2'- and 3'-AMP) have been determined by HPLC over a wide pH range. Both reactions proceed at comparable rates under acidic conditions, exhibiting a second-order dependence of rate on hydronium ion concentration at 1 < pH < 2, and a first-order dependence in more acidic solutions. Moreover, hydrolytic depurination takes place at pH < 3. In the pH range 4 to 9 a pH-independent phosphate migration prevails. By contrast, in alkaline solutions the methyl esters are hydrolyzed to a mixture of 2'- and 3'-AMP, the reaction rate being proportional to the hydroxide ion concentration at [OH-] < 0.1 mol dm-3. No sign of mutual isomerization was detected under these conditions. With the isopropyl esters alkaline degradation of the adenine moiety is considerably faster than the phosphodiester hydrolysis. Mechanisms of phosphate migration and phosphodiester hydrolysis under various conditions have been discussed.
• Brown et al., Journal of the Chemical Society, 1955, p. 4396,4399
  作者：Brown et al.

  DOI：——

  日期：——