4,7-diglutathionyl-5,6-dihydroxytryptamine | 132259-63-3

• 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: 4,7-diglutathionyl-5,6-dihydroxytryptamine
• 英文别名: (2S)-2-amino-5-[[(2S)-3-[[7-[(2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-3-(2-aminoethyl)-5,6-dihydroxy-1H-indol-4-yl]sulfanyl]-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 132259-63-3
• 化学式: C₃₀H₄₂N₈O₁₄S₂
• 分子量: 802.841
• InChiKey: IXKDPPRJQNEDKU-CAOSSQGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.98
• 重原子数：
  54.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  399.91
• 氢给体数：
  14.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-5-[[(2S)-3-[[3-(2-aminoethyl)-5,6-dioxo-1H-indol-4-yl]sulfanyl]-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid 、 4,7-diglutathionyl-5,6-dihydroxytryptamine 生成 4,7,4'-triglutathionyl-2,7'-bi(5,6-dihydroxytryptamine)
  参考文献：
  名称：

  SINGH, SATENDRA;DRYHURST, GLENN, J. ORG. CHEM., 56,(1991) N, C. 1767-1773

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S)-2-amino-5-[[(2S)-3-[[3-(2-aminoethyl)-5,6-dioxo-1H-indol-4-yl]sulfanyl]-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid 、 谷胱甘肽 生成 4,7-diglutathionyl-5,6-dihydroxytryptamine
  参考文献：
  名称：

  SINGH, SATENDRA;DRYHURST, GLENN, J. ORG. CHEM., 56,(1991) N, C. 1767-1773

  摘要：

  DOI：

文献信息

• Reactions of the serotonergic neurotoxin 5, 6-dihydroxytryptamine with glutathione
  作者：Satendra Singh、Glenn Dryhurst

  DOI：10.1021/jo00005a021

  日期：1991.3

  At physiological pH the serotonergic neurotoxin 5,6-dihydroxytryptamine (5,6-DHT) catalyzes the oxidation of the cellular antioxidant glutathione (GSH) by molecular oxygen to give GSSG. At the stage when GSH is depleted, 5,6-DHT is then autoxidized to give first 2,7'-bi(5,6-dihydroxytryptamine) (2) and ultimately indolic melanin. In the presence of an excess of GSH and enzymes such as tyrosinase or ceruloplasmin, the oxidation of 5,6-DHT to its corresponding o-quinone (1) is greatly accelerated. Under such conditions, 1 is attacked by GSH to give 4-S-glutathionyl-5,6-dihydroxytryptamine (A), which is further oxidized to the corresponding quinone 4. Further attack by GSH or A on 4 gives 4,7-diglutathionyl-5,6-dihydroxytryptamine (B) and 4,4'-di-S-glutathionyl-2,7'-bi(5,6-dihydroxytryptamine) (C), respectively. Reaction between 4 and B yields 4,7,4'-tri-S-glutathionyl-2,7'-bi(5,6-dihydroxytryptamine) (D).