3,4-dihydroxyphenylalanyl glycine | 37181-68-3

• 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: 3,4-dihydroxyphenylalanyl glycine
• 英文别名: Glycine, N-(3-hydroxy-L-tyrosyl)-；2-[[(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoyl]amino]acetic acid
• CAS: 37181-68-3
• 化学式: C₁₁H₁₄N₂O₅
• 分子量: 254.243
• InChiKey: URBGGMJZVAVPOH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  133
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-酪氨酰甘氨酸 在 EDTA 、 双氧水 、 sodium phosphate 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.08h， 生成 、 3,4-dihydroxyphenylalanyl glycine
  参考文献：
  名称：

  Superoxide Reaction with Tyrosyl Radicals Generates para-Hydroperoxy and para-Hydroxy Derivatives of Tyrosine

  摘要：

  Tyrosine-derived hydroperwddes are formed in peptides and proteins exposed to enzymatic or cellular sources of superoxide and oxidizing species as a result of the nearly diffusion-limited reaction between tyrosyl radical and superoxide. However, the structure of these products, which informs their reactivity in biology, has not been unequivocally established. We report here the complete characterization of the products formed in the addition of superoxide, generated from xanthine oxidase, to several peptide-derived tyrosyl radicals, formed from horseradish peroxidase. RP-HPLC, LC-MS, and NMR experiments indicate that the primary stable products of superoxide addition to tyrosyl radical are para-hydroperwdde derivatives (para relative to the position of the OH in tyrosine) that can be reduced to the corresponding para-alcohol. In the case of glycyl-tyrosine, a stable 3-(1-hydroperoxy-4-oxocyclohexa-2,5-dien-1-yl)-L-alanine was formed. In tyrosyl-glycine and Leu-enkephalin, which have N-terminal tyrosines, bicyclic indolic para-hydroperoxide derivatives were formed ((2S,3aR,7aR)-3a-hydroperoxy-6-oxo-2,3,3a,6,7,7a-hexahydro-1H-indole-2-carboxylic acid) by the conjugate addition of the free amine to the cyclohexadienone. It was also found that significant amounts of the para-OH derivative were generated from the hydroxyl radical, formed on exposure of tyrosine-containing peptides to Fenton conditions. The para-OOH and para-OH derivatives are much more reactive than other tyrosine oxidation products and may play important roles in physiology and disease.

  DOI：

  10.1021/ja307215z

文献信息

• US3939253A
  申请人：——

  公开号：US3939253A

  公开（公告）日：1976-02-17
• US3962457A
  申请人：——

  公开号：US3962457A

  公开（公告）日：1976-06-08
• US3998799A
  申请人：——

  公开号：US3998799A

  公开（公告）日：1976-12-21
• US4035507A
  申请人：——

  公开号：US4035507A

  公开（公告）日：1977-07-12
• US4065566A
  申请人：——

  公开号：US4065566A

  公开（公告）日：1977-12-27