<2-15N>-2'-deoxyguanosine | 121409-37-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: <2-15N>-2'-deoxyguanosine
• 英文别名: [15N²]deoxyguanosine；2-(15N)azanyl-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 121409-37-8
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 268.238
• InChiKey: YKBGVTZYEHREMT-KPBFQBRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  β-(benzoyloxy)acrolein 、 <2-15N>-2'-deoxyguanosine 在 sodium phosphate buffer 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Mechanism of Reaction of β-(Aryloxy)acroleins with Nucleosides

  摘要：

  The mechanism of DNA adduct formation by acroleins substituted with good leaving groups in the beta-position was investigated using [3-H-2]-3-(p-nitrophenoxy)acrolein (1). Reaction of 1 with guanosine at acidic pH produced 9-beta-D-ribofuranosylpyrimido[1,2-a]purin-10(3H)-one containing equal amounts of deuterium at both carbons 6 and 8, indicating that hydrolysis of 1 to beta-hydroxyacrolein (malondialdehyde) occurred prior to reaction with guanosine. In contrast, reaction of 1 with deoxyguanosine at neutral pH produced 9-(beta-o-2'-deoxyribofuranosyl)pyrimido[1,2-a]purin-10(3H)-one with deuterium selectively incorporated at position 8. This indicates that the pyrimido[1,2-a]purin-10(3H)-one adduct forms by 1,2-addition of the exocyclic amino group of deoxyguanosine to the aldehyde carbon of 1 followed by cyclization with the ring nitrogen. In concert with these observations, reaction of 1 with p-nitroaniline produced 3-[(p-nitrophenyl)amino]acrolein with deuterium exclusively in the aldehyde carbon. These observations define the chemical steps in DNA adduct formation by acroleins substituted at the beta-position with good leaving groups. In addition, they explain the relatively modest dependence of mutagenicity on leaving group ability in this series of compounds.

  DOI：

  10.1021/tx950105t
• 作为产物：
  描述：

  (2R,3S,5R)-5-[2-(15N)azanyl-6-(2-phenylsulfanylethoxy)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol 生成 <2-15N>-2'-deoxyguanosine
  参考文献：
  名称：

  KIEPER, INGO;SCHMIDT, THOMAS;FERA, BRIAN;RUTERJANS, HEINZ, NUCLEOSIDES AND NUCLEOTIDES, 7,(1988) N-6, C. 821-825

  摘要：

  DOI：

文献信息

• Nitrogen-15-labeled deoxynucleosides. 4. Synthesis of [1-15N] and [2-15N]-labeled 2'-deoxyguanosines
  作者：Bhaswati Goswami、Roger A. Jones

  DOI：10.1021/ja00002a037

  日期：1991.1

  The syntheses of [1- 15 N]- and [2- 15 N]-2'-deoxyguanosines are reported via transformation of 2'-deoxyadenosine. The 15 N source for the [1- 15 N] label is [6- 15 N]-2'-deoxyadenosine, while for the [2- 15 N] label it is [ 15 N]KCN. The synthetic route is particularly straightforward in that there are no protection and deprotection steps and only one chromatographic purification. Furthermore, it

  [1- 15 N]-和[2- 15 N]-2'-脱氧鸟苷的合成是通过2'-脱氧腺苷的转化报道的。[1- 15 N] 标签的 15 N 来源是 [6- 15 N]-2'-脱氧腺苷，而 [2- 15 N] 标签的 15 N 来源是 [ 15 N] KCN。合成路线特别简单，没有保护和脱保护步骤，只有一个色谱纯化。此外，它直接适用于标记核糖核苷的制备
• KIEPER, INGO;SCHMIDT, THOMAS;FERA, BRIAN;RUTERJANS, HEINZ, NUCLEOSIDES AND NUCLEOTIDES, 7,(1988) N-6, C. 821-825
  作者：KIEPER, INGO、SCHMIDT, THOMAS、FERA, BRIAN、RUTERJANS, HEINZ

  DOI：——

  日期：——
• GOSWAMI, BHASWATI;JONES, ROGER A., J. AMER. CHEM. SOC., 113,(1991) N, C. 644-647
  作者：GOSWAMI, BHASWATI、JONES, ROGER A.

  DOI：——

  日期：——
• Mechanism of Reaction of β-(Aryloxy)acroleins with Nucleosides
  作者：G. Ramachandra Reddy、Lawrence J. Marnett

  DOI：10.1021/tx950105t

  日期：1996.1.1

  The mechanism of DNA adduct formation by acroleins substituted with good leaving groups in the beta-position was investigated using [3-H-2]-3-(p-nitrophenoxy)acrolein (1). Reaction of 1 with guanosine at acidic pH produced 9-beta-D-ribofuranosylpyrimido[1,2-a]purin-10(3H)-one containing equal amounts of deuterium at both carbons 6 and 8, indicating that hydrolysis of 1 to beta-hydroxyacrolein (malondialdehyde) occurred prior to reaction with guanosine. In contrast, reaction of 1 with deoxyguanosine at neutral pH produced 9-(beta-o-2'-deoxyribofuranosyl)pyrimido[1,2-a]purin-10(3H)-one with deuterium selectively incorporated at position 8. This indicates that the pyrimido[1,2-a]purin-10(3H)-one adduct forms by 1,2-addition of the exocyclic amino group of deoxyguanosine to the aldehyde carbon of 1 followed by cyclization with the ring nitrogen. In concert with these observations, reaction of 1 with p-nitroaniline produced 3-[(p-nitrophenyl)amino]acrolein with deuterium exclusively in the aldehyde carbon. These observations define the chemical steps in DNA adduct formation by acroleins substituted at the beta-position with good leaving groups. In addition, they explain the relatively modest dependence of mutagenicity on leaving group ability in this series of compounds.