四氢蝶酰五谷氨酸酯 | 41520-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 中文名称: 四氢蝶酰五谷氨酸酯
• 英文名称: (2S)-2-[[(4S)-4-[[(4S)-4-[[(4S)-4-[[(4S)-4-[[4-[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methylamino]benzoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]pentanedioic acid
• CAS: 41520-73-4
• 化学式: C₃₉H₅₁N₁₁O₁₈
• 分子量: 961.897
• InChiKey: MEFNETHLDFHDHW-XIEHAMPZSA-N

物化性质

• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  68
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  473
• 氢给体数：
  16
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  蝶酰五联谷氨酸 在 sodium tetrahydroborate 、 lead(II) nitrate 作用下， 生成 四氢蝶酰五谷氨酸酯
  参考文献：
  名称：

  Histone Demethylase LSD1 Is a Folate-Binding Protein

  摘要：

  Methylation of lysine residues in histones has been known to serve a regulatory role in gene expression. Although enzymatic removal of the methyl groups was discovered as early as 1973, the enzymes responsible for their removal were isolated and their mechanism of action was described only recently. The first enzyme to show such activity was LSD1, a flavin-containing enzyme that removes the methyl groups from lysines 4 and 9 of histone 3 with the generation of formaldehyde from the methyl group. This reaction is similar to the previously described demethylation reactions conducted by the enzymes dimethylglycine dehydrogenase and sarcosine dehydrogenase, in which protein-bound tetrahydrofolate serves as an accepter of the formaldehyde that is generated. We now show that nuclear extracts of HeLa cells contain LSD1 that is associated with folate. Using the method of back-scattering interferometry, we have measured the binding of various forms of folate to both full-length LSD1 and a truncated form of LSD1 in free solution. The 6R,S form of the natural pentaglutamate form of tetrahydrofolate bound with the highest affinity (K-d = 2.8 mu M) to full-length LSD1. The fact that folate participates in the enzymatic demethylation of histones provides an opportunity for this micronutrient to play a role in the epigenetic control of gene expression.

  DOI：

  10.1021/bi200247b