7-[(2S)-2-amino-2-carboxyethyl]-5-hydroxy-3,4-dihydro-2H-1,4-benzothiazine-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 7-[(2S)-2-amino-2-carboxyethyl]-5-hydroxy-3,4-dihydro-2H-1,4-benzothiazine-3-carboxylic acid
• 化学式: C₁₂H₁₄N₂O₅S
• 分子量: 298.32
• InChiKey: ACUWXAUSGNGBKQ-PKPIPKONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  半胱氨酰多巴 在 phosphate buffer 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 生成 7-(2-amino-2-carboxyethyl)-5-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzothiazine 、 (2S)-2-amino-3-(5-hydroxy-3,4-dihydro-2H-1,4-benzothiazin-7-yl)propanoic acid 、 7-(2-amino-2-carboxyethyl)-3,5-dihydroxy-3,4-dihydro-2H-1,4-benzothiazine 、 7-[(2S)-2-amino-2-carboxyethyl]-5-hydroxy-3,4-dihydro-2H-1,4-benzothiazine-3-carboxylic acid
  参考文献：
  名称：

  A New Insight in the Biosynthesis of Pheomelanins:  Characterization of a Labile 1,4-Benzothiazine Intermediate

  摘要：

  It has long been known that pheomelanins, the distinctive pigments of red hair and celtic skin, arise by the oxidative cyclization of cysteinyldopas, mainly the 5-S-isomer 1, via 1,4-benzothiazines. However, the nature and reactivity of these intermediates have remained poorly defined. In an reexamination of the oxidation of 1, in aqueous buffers at physiological pHs, a hitherto unknown labile intermediate was identified and formulated as the 3-hydroxy-3,4-dihydro-1,4-benzothiazine 5 based on direct NMR analysis of the reaction mixture and conversion to the stable benzothiazines 3 and 4 under different conditions. Structure 5 was further supported by oxidation of the model compound 6 leading to the analogous more stable 2,2-dimethyldihydro-1,4-benzothiazine 9.

  DOI：

  10.1021/jo981018j

文献信息

• A New Insight in the Biosynthesis of Pheomelanins:  Characterization of a Labile 1,4-Benzothiazine Intermediate
  作者：Alessandra Napolitano、Sofia Memoli、Giuseppe Prota

  DOI：10.1021/jo981018j

  日期：1999.4.1

  It has long been known that pheomelanins, the distinctive pigments of red hair and celtic skin, arise by the oxidative cyclization of cysteinyldopas, mainly the 5-S-isomer 1, via 1,4-benzothiazines. However, the nature and reactivity of these intermediates have remained poorly defined. In an reexamination of the oxidation of 1, in aqueous buffers at physiological pHs, a hitherto unknown labile intermediate was identified and formulated as the 3-hydroxy-3,4-dihydro-1,4-benzothiazine 5 based on direct NMR analysis of the reaction mixture and conversion to the stable benzothiazines 3 and 4 under different conditions. Structure 5 was further supported by oxidation of the model compound 6 leading to the analogous more stable 2,2-dimethyldihydro-1,4-benzothiazine 9.