N-β-alanyldopamine | 58077-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-β-alanyldopamine
• 英文别名: N-beta-alanyldopamine (hydrochloride)；3-amino-N-[2-(3,4-dihydroxyphenyl)ethyl]propanamide;hydrochloride
• CAS: 58077-93-3
• 化学式: C₁₁H₁₆N₂O₃*ClH
• 分子量: 260.721
• InChiKey: LLFAHTAIALXURP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  95.6
• 氢给体数：
  5
• 氢受体数：
  4

制备方法与用途

生物活性

N-β-alanyldopamine hydrochloride (NBAD hydrochloride) 是血淋巴中多巴胺的主要衍生物。

反应信息

• 作为产物：
  描述：

  t-butyloxycarbonyl-β-alanyldopamine 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以95%的产率得到N-β-alanyldopamine
  参考文献：
  名称：

  A convenient method for the preparation of N-.BETA.-alanyldopamine as a substrate of phenoloxidase.

  摘要：

  DOI：

  10.1271/bbb1961.54.833

文献信息

• Model Insect Cuticle Sclerotization: Reactions of Catecholamine Quinones with the Nitrogen-Centered Nucleophiles Imidazole andN-Acetylhistidine
  作者：Xin Huang、Rongda Xu、M.Dale Hawley、Karl J. Kramer

  DOI：10.1006/bioo.1997.1065

  日期：1997.6

  The catecholamines N-acetyldopamine (NADA) and N-beta-alanyldopamine (NBAD) are two precursors for quinonoios used as sclerotizing agents in insect cuticle. This study focused on the reaction pathways of the quinones of NADA and NBAD by using two nitrogen-centered nucleophiles, imidazole and N-acetylhistidine, to model cuticular proteins containing histidyl residues. The quinones were prepared by electrochemical oxidation, using either a coulometric microcell or a how-through cell. The reactions of the quinones with the nucleophiles were investigated at physiological pH using electrochemical, chromatographic, and spectroscopic methods. The major products were purified by semipreparative Liquid chromatography and identified by mass spectrometry and nuclear magnetic resonance spectroscopy to be nucleophilic addition products of the quinones with the nucleophiles bonded to two carbons in the aromatic ring. The predominant products for both nucleophiles were C6 adducts of NADA and NBAD. C2 adducts of N-acetylhistidine were minor products. (C) 1997 Academic Press.