(S)-2-Amino-4-[(R)-2-[3-((S)-2-amino-2-carboxy-ethyl)-4,5-dioxo-4,5-dihydro-1H-indol-7-ylsulfanyl]-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid | 182007-53-0

• 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)-2-Amino-4-[(R)-2-[3-((S)-2-amino-2-carboxy-ethyl)-4,5-dioxo-4,5-dihydro-1H-indol-7-ylsulfanyl]-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid
• CAS: 182007-53-0
• 化学式: C₂₁H₂₅N₅O₁₀S
• 分子量: 539.523
• InChiKey: MQGIBWWBOPMSTD-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.31
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  272.07
• 氢给体数：
  8.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-4-[(R)-2-[3-((S)-2-amino-2-carboxy-ethyl)-4,5-dioxo-4,5-dihydro-1H-indol-7-ylsulfanyl]-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid 在 ammonium hydroxide 、 air 作用下， 生成 6,8-bi-S-glutathionyl-α-amino-10,11-dihydro-10,11-dioxo-11bH-indolo[2',3':4,5]furo[3,2-h]pyrrolo(4,3,2-de)quinoline-11b-propanoic acid 、 6,8-bi-S-glutathionyl-α-amino-2-carboxy-10,11-dihydro-10,11-dioxo-11bH-indolo[2',3':4,5]furo[3,2-h]pyrrolo(4,3,2-de)quinoline-11b-propanoic acid
  参考文献：
  名称：

  7-S-Glutathionyltryptophan-4,5-dione: Formation from 5-Hydroxytryptophan and Reactions with Glutathione

  摘要：

  The electrochemically driven oxidation of 5-hydroxytryptophan (5-HTPP) in the presence of free glutathione (GSH) yields 4-S-glutathionyl-5-hydroxytryptophan (5) and 7S-glutathionyltryptophan-4,5-dione (7). The latter glutathionyl conjugate is formed both by nucleophilic addition of GSH to tryptophan-4,5-dione (4), a normal product of the oxidation of 5-HTPP, and by oxidation of 5 in a reaction where the glutathionyl residue migrates from the C(4)- to the C(7)-position. In the presence of free GSH 7 reacts to give the 3,7- and 6,7-bi-S-glutathionyl conjugates of 4 and, as a result of intramolecular cyclization reactions, a number of glutathionyl conjugates of an unusual tricyclic pyrroloquinoline. It is speculated that one or more of these products might represent aberrant oxidative metabolites that have been detected in the cerebrospinal fluid of patients with Alzheimer's Disease. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0012
• 作为产物：
  描述：

  5-羟基-L-色氨酸 在 盐酸 、 ammonium hydroxide 、 溶剂黄146 作用下， 生成 (S)-2-Amino-4-[(R)-2-[3-((S)-2-amino-2-carboxy-ethyl)-4,5-dioxo-4,5-dihydro-1H-indol-7-ylsulfanyl]-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid
  参考文献：
  名称：

  7-S-Glutathionyltryptophan-4,5-dione: Formation from 5-Hydroxytryptophan and Reactions with Glutathione

  摘要：

  The electrochemically driven oxidation of 5-hydroxytryptophan (5-HTPP) in the presence of free glutathione (GSH) yields 4-S-glutathionyl-5-hydroxytryptophan (5) and 7S-glutathionyltryptophan-4,5-dione (7). The latter glutathionyl conjugate is formed both by nucleophilic addition of GSH to tryptophan-4,5-dione (4), a normal product of the oxidation of 5-HTPP, and by oxidation of 5 in a reaction where the glutathionyl residue migrates from the C(4)- to the C(7)-position. In the presence of free GSH 7 reacts to give the 3,7- and 6,7-bi-S-glutathionyl conjugates of 4 and, as a result of intramolecular cyclization reactions, a number of glutathionyl conjugates of an unusual tricyclic pyrroloquinoline. It is speculated that one or more of these products might represent aberrant oxidative metabolites that have been detected in the cerebrospinal fluid of patients with Alzheimer's Disease. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0012