S-[1-(N2-deoxyguanosinyl)-methyl]glutathione | 152406-76-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-[1-(N2-deoxyguanosinyl)-methyl]glutathione
• 英文别名: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[[[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]amino]methylsulfanyl]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 152406-76-3
• 化学式: C₂₁H₃₀N₈O₁₀S
• 分子量: 586.583
• InChiKey: FWVYUWNLJGZLRO-ZXPJVPCYSA-N

物化性质

• 密度：
  1.85±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  305
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2'-脱氧鸟苷 、 (2S)-2-氨基-5-[[(2R)-1-(羧甲基氨基)-3-(羟基甲硫基)-1-氧代丙烷-2-基]氨基]-5-氧代戊酸 反应 8.0h， 生成 S-[1-(N2-deoxyguanosinyl)-methyl]glutathione
  参考文献：
  名称：

  Formation of S-[1-(N²-Deoxyguanosinyl)methyl]glutathione between Glutathione and DNA Induced by Formaldehyde

  摘要：

  Formaldehyde is an essential metabolic intermediate in human cells and can also enter into the body through environmental, exposures. It is classified as a human and animal carcinogen according to the International Agency for Research on Cancer (IARC). Previous research has demonstrated that formaldehyde is genotoxic, causing mutations in multiple genes. However, no exogenous formaldehyde-induced DNA adducts have been detected in animals after inhalation exposure, although formaldehyde can result in N-6-deoxyadenosine, N-2-deoxyguanosine, and N-4-deoxycytidine adducts in vitro. This can be partially attributed to the rapid metabolism of formaldehyde by glutathione (GSH)dependent enzyme systems. Among the intermediates in the pathway of formaldehyde detoxication, S-hydroxymethylglutathione is a reactive species and has the potential to further conjugate with DNA bases. Here, we have demonstrated the formation of S-[1-(N-2-deoxyguanosinyl) methyl]glutathione between glutathione and DNA in the presence of formaldehyde. This adduct is unique because of the involvement of S-hydroxymethylglutathione which is a key player during the detoxication of formaldehyde.

  DOI：

  10.1021/ja808048c