N-acetyl-N-nitrosotryptophan | 958778-99-9

• 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-N-nitrosotryptophan
• 英文别名: NO-AcTrp；N-Acetyl-N'-nitrosotryptophan；(2S)-2-[acetyl(nitroso)amino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 958778-99-9
• 化学式: C₁₃H₁₃N₃O₄
• 分子量: 275.264
• InChiKey: QGCFCYSWAISKFH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-乙酰-L-色氨酸 在 尿酸 、 1,1-diethyl-2-hydroxy-2-nitrosohydrazine 作用下， 生成 N-acetyl-N-nitrosotryptophan
  参考文献：
  名称：

  尿酸对二乙胺NONOate和N-乙酰基-N-亚硝基色氨酸亚硝化N-乙酰基半胱氨酸的影响。

  摘要：

  人血浆浓度的尿酸可在中性pH值下促进二乙胺NONOate对N-乙酰半胱氨酸的亚硝化作用，但可减少N-乙酰色氨酸的亚硝化作用。尿酸还通过在吲哚环的氮原子上具有亚硝基的N-乙酰基-N-亚硝基色氨酸加速了N-乙酰基半胱氨酸的亚硝化。即使在中性pH下存在尿酸和N-乙酰基色氨酸，N-乙酰基-S-亚硝基半胱氨酸也是稳定的，而尿酸和N-乙酰基半胱氨酸可促进N-乙酰基-N-亚硝基色氨酸的分解。结果表明，尿酸从二乙胺NONOate或N-乙酰基-N-亚硝基色氨酸中获得亚硝基，并将其传递至N-乙酰基半胱氨酸的巯基，从而得到N-乙酰基-S-亚硝基半胱氨酸。

  DOI：

  10.1248/cpb.57.736

文献信息

• [EN] METHODS FOR THE REVERSIBLE PROTECTION OF PROTEINS DURING PATHOGEN INACTIVATION<br/>[FR] METHODES DE PROTECTION REVERSIBLE DE PROTEINES PENDANT L'INACTIVATION PATHOGENE
  申请人：NAT BLOOD AUTHORITY

  公开号：WO2006005961A1

  公开（公告）日：2006-01-19

  The present invention relates to a method for the in vitro reversible protection of a protein comprising the nitrosylation of reactive sites in said protein. Methods of protein processing or purification; methods of maintaining the structure and/or function of a protein during exposure of said protein to reactive species and/or physical processing steps; and methods of virus inactivation in a protein sample comprising the method for the in vitro reversible protection of a protein are also described. A method for protein disulphide bond formation comprising nitrosylating a free thiol group in a protein to form a nitrosothiol group, and then exposing the protein to conditions which promote disulphide bond formation between two nitrosothiol groups is provided. Proteins obtainable by the methods of the invention and kits for carrying out the methods of the invention are also described
• Effects of Uric Acid on Nitrosation of &lt;i&gt;N&lt;/i&gt;-Acetylcysteine by Diethylamine NONOate and &lt;i&gt;N&lt;/i&gt;-Acetyl-&lt;i&gt;N&lt;/i&gt;-nitrosotryptophan
  作者：Toshinori Suzuki、Atsushi Naka、Haruka Kimura

  DOI：10.1248/cpb.57.736

  日期：——

  N-acetylcysteine by diethylamine NONOate at neutral pH, but diminished that of N-acetyltryptophan. Uric acid also accelerated nitrosation of N-acetylcysteine by N-acetyl-N-nitrosotryptophan, having a nitroso group on the nitrogen atom of the indole ring. N-Acetyl-S-nitrosocysteine was stable even in the presence of uric acid and N-acetyltryptophan at neutral pH, while decomposition of N-acetyl-N-nitrosotryptophan

  人血浆浓度的尿酸可在中性pH值下促进二乙胺NONOate对N-乙酰半胱氨酸的亚硝化作用，但可减少N-乙酰色氨酸的亚硝化作用。尿酸还通过在吲哚环的氮原子上具有亚硝基的N-乙酰基-N-亚硝基色氨酸加速了N-乙酰基半胱氨酸的亚硝化。即使在中性pH下存在尿酸和N-乙酰基色氨酸，N-乙酰基-S-亚硝基半胱氨酸也是稳定的，而尿酸和N-乙酰基半胱氨酸可促进N-乙酰基-N-亚硝基色氨酸的分解。结果表明，尿酸从二乙胺NONOate或N-乙酰基-N-亚硝基色氨酸中获得亚硝基，并将其传递至N-乙酰基半胱氨酸的巯基，从而得到N-乙酰基-S-亚硝基半胱氨酸。