N-acetyl-6-oxo-L-norleucine

• 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: N-acetyl-6-oxo-L-norleucine
• 英文别名: (2S)-2-acetamido-6-oxohexanoic acid
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: CRVYRJLIQHSUOQ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-6-oxo-L-norleucine 、 对氨基苯甲酸 在 sodium cyanoborohydride 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Antioxidant and pro-oxidant actions of resveratrol on human serum albumin in the presence of toxic diabetes metabolites: Glyoxal and methyl-glyoxal

  摘要：

  Methylglyoxal (MGO) and glyoxal (GO) are attracting considerable attention because of their role in the onset of diabetes symptoms. Therefore, to comprehend the molecular fundamentals of their pathological actions is of the utmost importance. In this study, the molecular interactions between resveratrol (RES) and human serum albumin (HSA) and the ability of the stilbene to counteract the oxidative damage caused by pathological concentrations of MGO and GO to the human plasma protein, was assessed. The oxidation of Cys34 in HSA as well as the formation of specific protein semialdehydes AAS (alpha-aminoadipic), GGS (gamma-glutamic) and the accumulation of Advanced Glycation End-products (AGEs) was investigated. Resveratrol was found to neutralize both alpha-di-carbonyls by forming adducts detected by HESI-Orbitrap-MS. This antioxidant action was manifested in a significant reduction of AGEs. However, RES-alpha-dicarbonyl conjugates oxidized Cys34 and lysine, arginine and/or proline by a nucleophilic attack on SH and epsilon-NH groups in HSA. The formation of specific semialdehydes in HSA after incubation with GO and MGO at pathological concentrations was reported for the first time in this study, and may be used as early and specific biomarkers of the oxidative stress undergone by diabetic patients. The pro oxidative role of the RES-alpha-dicarbonyl conjugates should be further investigated to clarify whether this action leads to positive or harmful clinical consequences. The biological relevance of human protein carbonylation as a redox signaling mechanism and/or as a reflection of oxidative damage and disease should also be studied in future works.

  DOI：

  10.1016/j.bbagen.2018.06.007
• 作为产物：
  描述：

  N-乙酰-L-赖氨酸 在 egg shell membrane 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 生成 N-acetyl-6-oxo-L-norleucine
  参考文献：
  名称：

  赖氨酸氧化终产物α-氨基己二酸对益生菌罗伊氏乳杆菌PL503氧化还原状态和基因表达影响的体外测定

  摘要：

  本研究旨在获取有关食物中游离氧化氨基酸 α-氨基己二酸 (AAA) 对益生菌罗伊氏乳杆菌PL503 影响的潜在机制的信息。该细菌在结肠模拟条件下（微需氧条件下 37°C 24 小时）孵育，并暴露于三种食品相容的 AAA 浓度，即 1 mM、5 mM 和 10 mM。还考虑了没有 AAA 暴露的对照组。四个实验条件中的每一个重复 3 次，并在 12、16、20 和 24 小时收集样品。AAA 对uspA基因的下调（与对照相比减少了 0.5 倍）表明 AAA 被确定为潜在的化学威胁。dhaT _与抗氧化防御有关的基因被发现在用 1 和 5 mM AAA 处理的细菌中上调（与对照相比增加了两倍），这表明氧化氨基酸能够削弱氧化还原状态的能力。细菌。事实上，AAA 导致罗伊氏乳杆菌中活性氧 (ROS) 的产生增加和翻译后变化（蛋白质羰基化）的增加（高达 13 nmol 赖氨酸/mg 蛋白质，而对照组为

  DOI：

  10.1007/s00726-021-03087-4