3-<(S)-2-amino-2-carboxy-1,1-dimethylethylthio>-5-<(S)-2-amino-2-carboxyethyl>-1,2-dihydroxybenzene | 228120-24-9

• 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: 3-<(S)-2-amino-2-carboxy-1,1-dimethylethylthio>-5-<(S)-2-amino-2-carboxyethyl>-1,2-dihydroxybenzene
• 英文别名: (2S)-2-amino-3-[5-[(2S)-2-amino-2-carboxyethyl]-2,3-dihydroxyphenyl]sulfanyl-3-methylbutanoic acid
• CAS: 228120-24-9
• 化学式: C₁₄H₂₀N₂O₆S
• 分子量: 344.389
• InChiKey: KEWVOOUADWHWAJ-CPCISQLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-<(S)-2-amino-2-carboxy-1,1-dimethylethylthio>-5-<(S)-2-amino-2-carboxyethyl>-1,2-dihydroxybenzene 在 sodium tetrahydroborate 、 phosphate buffer 、 potassium hexacyanoferrate(III) 作用下， 生成 7-(2-amino-2-carboxyethyl)-5-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1,4-benzothiazine
  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
• 作为产物：
  描述：

  D-青霉胺 、 左旋多巴 在 ammonium cerium(IV) nitrate 、 硫酸 作用下， 反应 0.17h， 生成 3-<(S)-2-amino-2-carboxy-1,1-dimethylethylthio>-5-<(S)-2-amino-2-carboxyethyl>-1,2-dihydroxybenzene
  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