(4R,7S,10R)-10-((S)-4-Amino-4-carboxy-butyrylamino)-7-carboxymethyl-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carboxylic acid | 581799-95-3

• 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: (4R,7S,10R)-10-((S)-4-Amino-4-carboxy-butyrylamino)-7-carboxymethyl-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carboxylic acid
• CAS: 581799-95-3
• 化学式: C₁₅H₂₂N₄O₉S₂
• 分子量: 466.493
• InChiKey: MCCUCFAMESWLBF-JBDRJPRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.41
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  225.22
• 氢给体数：
  7.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (4R,7S,10R)-10-((S)-4-Amino-4-carboxy-butyrylamino)-7-carboxymethyl-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carboxylic acid 在 ammonium hydroxide 、 三丁基膦 作用下， 以 丙醇 、 水 为溶剂， 反应 1.0h， 以70%的产率得到(S)-2-Amino-4-{(R)-1-[(S)-2-carboxy-1-((R)-1-carboxy-2-mercapto-ethylcarbamoyl)-ethylcarbamoyl]-2-mercapto-ethylcarbamoyl}-butyric acid
  参考文献：
  名称：

  Synthesis and biological evaluation of the disulfide form of the glutathione analogue γ-(l-glutamyl)-l-cysteinyl-l-aspartyl-l-cysteine

  摘要：

  By using the chain to chain mode of cyclization the title glutathione analogue (gammaGlu-Cys-Asp-Cys) (4), containing the 11-membered disulfide ring (Cys-Asp-Cys) replacing the native -Cys-Gly fragment, has been synthesized and characterized together with its reduced dithiol form gamma-Glu-Cys-Asp-Cys (5). The activity of (4) with gamma-glutamyl-transferase and glutathione reductase has been evaluated and compared with those of the two conformationally restricted glutathione analogues (2) and (3) previously reported. (C) 2003 Elsevier Science (USA). All rights reserved.

  DOI：

  10.1016/s0045-2068(03)00022-1
• 作为产物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-4-{(R)-1-[(S)-2-tert-butoxycarbonyl-1-((R)-1-tert-butoxycarbonyl-2-tritylsulfanyl-ethylcarbamoyl)-ethylcarbamoyl]-2-tritylsulfanyl-ethylcarbamoyl}-butyric acid tert-butyl ester 在 盐酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.5h， 生成 (4R,7S,10R)-10-((S)-4-Amino-4-carboxy-butyrylamino)-7-carboxymethyl-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of the disulfide form of the glutathione analogue γ-(l-glutamyl)-l-cysteinyl-l-aspartyl-l-cysteine

  摘要：

  By using the chain to chain mode of cyclization the title glutathione analogue (gammaGlu-Cys-Asp-Cys) (4), containing the 11-membered disulfide ring (Cys-Asp-Cys) replacing the native -Cys-Gly fragment, has been synthesized and characterized together with its reduced dithiol form gamma-Glu-Cys-Asp-Cys (5). The activity of (4) with gamma-glutamyl-transferase and glutathione reductase has been evaluated and compared with those of the two conformationally restricted glutathione analogues (2) and (3) previously reported. (C) 2003 Elsevier Science (USA). All rights reserved.

  DOI：

  10.1016/s0045-2068(03)00022-1