2-(3,4-dihydroxyphenyl)-2-S-glutathionylacetaldehyde oxime

• 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: 2-(3,4-dihydroxyphenyl)-2-S-glutathionylacetaldehyde oxime
• 英文别名: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-[(2Z)-1-(3,4-dihydroxyphenyl)-2-hydroxyiminoethyl]sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• 化学式: C₁₈H₂₄N₄O₉S
• 分子量: 472.476
• InChiKey: CKCFGHMFJKYYGY-MPMMNQARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  257
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  谷胱甘肽 、 TRANS-咖啡酸 在 acetate buffer 、 氧化亚氮 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(3,4-dihydroxyphenyl)-2-S-glutathionylacetaldehyde oxime 、 2-(3,4-dihydroxyphenyl)-2-S-glutathionylacetaldehyde oxime
  参考文献：
  名称：

  Nitrite-Mediated decarboxylative conjugation of caffeic acid with glutathione under mildly acidic conditions

  摘要：

  In acetate buffer, pH 4, at room temperature, nitrite ions can mediate an unusual decarboxylative conjugation of caffeic acid with glutathione leading to novel isomeric 2-(3,4-dihydroxyphenyl)-2-S-glutathionylacetaldehyde oximes. These results hint at a possible role of endogenous and/or dietary glutathione in the mechanisms by which caffeic acid can affect the burden of carcinogenic N-nitroso compounds in the digestive tract. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00795-3

文献信息

• Nitrite-Mediated decarboxylative conjugation of caffeic acid with glutathione under mildly acidic conditions
  作者：Lucia Panzella、Alessandra Napolitano、Marco d'Ischia

  DOI：10.1016/s0960-894x(02)00795-3

  日期：2002.12

  In acetate buffer, pH 4, at room temperature, nitrite ions can mediate an unusual decarboxylative conjugation of caffeic acid with glutathione leading to novel isomeric 2-(3,4-dihydroxyphenyl)-2-S-glutathionylacetaldehyde oximes. These results hint at a possible role of endogenous and/or dietary glutathione in the mechanisms by which caffeic acid can affect the burden of carcinogenic N-nitroso compounds in the digestive tract. (C) 2002 Elsevier Science Ltd. All rights reserved.