2-S-半胱氨酰多巴 | 25565-17-7

• 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
• 中文名称: 2-S-半胱氨酰多巴
• 英文名称: 2-S-cysteinyl-3,4-dihydroxyphenylalanine
• 英文别名: (2S)-2-azaniumyl-3-[2-[(2R)-2-azaniumyl-2-carboxylatoethyl]sulfanyl-3,4-dihydroxyphenyl]propanoate
• CAS: 25565-17-7
• 化学式: C₁₂H₁₆N₂O₆S
• 分子量: 316.335
• InChiKey: IAGPESOLVJAEAG-BQBZGAKWSA-N

物化性质

• 沸点：
  593.2±50.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-S-半胱氨酰多巴 在 zinc(II) sulfate heptahydrate 、 potassium hexacyanoferrate(III) 、 盐酸 、 sodium persulfate 作用下， 以 水 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  Biologically inspired one-pot access routes to 4-hydroxybenzothiazole amino acids, red hair-specific markers of UV susceptibility and skin cancer risk

  摘要：

  The first practical access to 4-hydroxy-6-(2-amino-2-carboxyethyl)benzothiazole and 4-hydroxy-7-(2-amino-2-carboxyethyl)benzothiazole (1b and 2b) and the corresponding 2-carboxy-derivatives 1a and 2a is reported, involving one-pot sequential Zn2+-assisted biomimetic oxidation Of L-dopa and L-cysteine, 5-S-cysteinyldopa or 2-S-cysteinyldopa. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.041
• 作为产物：
  描述：

  在 盐酸 作用下， 反应 5.0h， 生成 2-S-半胱氨酰多巴
  参考文献：
  名称：

  The first expedient entry to the human melanogen 2-S-cysteinyldopa exploiting the anomalous regioselectivity of 3,4-dihydroxycinnamic acid–thiol conjugation

  摘要：

  The first convenient synthesis of 2-S-cysteinyl-3,4-dihydroxyphenylalanine (2-S-cysteinyldopa) in 30% overall yield is reported, which capitalizes on the anomalous regiochemistry of the oxidative coupling of 3,4-dihydroxycinnamic acid derivatives with thiol compounds, leading to 2-S rather than the usual 5-S conjugates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.098

文献信息

• Synthesis and antitumor activity of cysteinyl-3,4-dihydroxyphenylalonines and related compounds
  作者：Shosuke Ito、Shigeki Inoue、Yoshinobu Yamamoto、Keisuke Fujita

  DOI：10.1021/jm00138a006

  日期：1981.6

  exhibited antitumor activity against L1210 leukemia and B-16 melanoma in mice at doses which were not toxic to the host. Structural analogues of 5-S-cysteinyl-3,4-dihydroxyphenylalanine including several new compounds, were synthesized and tested for growth inhibition of cultured cells of human neuroblastoma YT-nu and Chinese hamster fibroblasts Don-6. Some were also examined for antitumor activity against

  天然的儿茶酚氨基酸5-S-半胱氨酰-3,4-二羟基苯丙氨酸（1）对培养的多种人类肿瘤细胞系具有选择性毒性，并在小鼠体内以L1210白血病和B-16黑色素瘤表现出抗肿瘤活性。对宿主无毒。合成了5-S-半胱氨酰基-3,4-二羟基苯丙氨酸的结构类似物，包括几种新化合物，并测试了其对人神经母细胞瘤YT-nu和中国仓鼠成纤维细胞Don-6培养细胞的生长抑制作用。还检查了一些体内抗L1210和B-16的抗肿瘤活性。通过邻苯二酚和苯酚与胱氨酸和沸腾的HBr水溶液反应，合成了无法通过常规方法制备的4-S-半胱氨酰邻苯二酚和2-和4-S-半胱氨酸苯酚。5-S-半胱氨酸-和2-S-半胱氨酸-3,4-二羟基苯丙氨酸（1和2），L-3,4-二羟基苯丙氨酸（L-Dopa）以及2-和4-S-半胱氨酰苯酚（14和15）仅对YT-nu细胞系有毒，而4-S-半胱氨酰邻苯二酚（6），3- S-半胱氨酰-5-甲基邻苯二酚（8）
• One-step Synthesis of (2-Amino-2-carboxyethylthio)dopas (Cys-dopas) from Dopa and Cysteine by Hydrogen Peroxide in the Presence of Iron–EDTA Complex
  作者：Shosuke Ito

  DOI：10.1246/bcsj.56.365

  日期：1983.1

  5-(2-Amino-2-carboxyethylthio)dopa, 2-(2-amino-2-carboxyethylthio)dopa, and 2,5-bis(2-amino-2-carboxyethylthio)dopa were synthesized from dopa and cysteine by oxidation in a neutral buffer with H2O2 in the presence of iron–EDTA complex. H2O2, iron salt, and EDTA were essential for the reaction. Ultimate oxidizing species seem to be hydroxyl and superoxide radicals.

  在中性缓冲液中，在铁-EDTA 复合物的存在下，用 H2O2 氧化多巴和半胱氨酸，合成了 5-(2-氨基-2-羧基乙硫基)多巴、2-(2-氨基-2-羧基乙硫基)多巴和 2,5-双(2-氨基-2-羧基乙硫基)多巴。H2O2、铁盐和 EDTA 对反应至关重要。最终氧化物种似乎是羟基和超氧自由基。
• The first expedient entry to the human melanogen 2-S-cysteinyldopa exploiting the anomalous regioselectivity of 3,4-dihydroxycinnamic acid–thiol conjugation
  作者：Lucia Panzella、Maria De Lucia、Alessandra Napolitano、Marco d’Ischia

  DOI：10.1016/j.tetlet.2007.08.098

  日期：2007.10

  The first convenient synthesis of 2-S-cysteinyl-3,4-dihydroxyphenylalanine (2-S-cysteinyldopa) in 30% overall yield is reported, which capitalizes on the anomalous regiochemistry of the oxidative coupling of 3,4-dihydroxycinnamic acid derivatives with thiol compounds, leading to 2-S rather than the usual 5-S conjugates. (C) 2007 Elsevier Ltd. All rights reserved.
• Biologically inspired one-pot access routes to 4-hydroxybenzothiazole amino acids, red hair-specific markers of UV susceptibility and skin cancer risk
  作者：Giorgia Greco、Lucia Panzella、Alessandra Napolitano、Marco d’Ischia

  DOI：10.1016/j.tetlet.2009.04.041

  日期：2009.6

  The first practical access to 4-hydroxy-6-(2-amino-2-carboxyethyl)benzothiazole and 4-hydroxy-7-(2-amino-2-carboxyethyl)benzothiazole (1b and 2b) and the corresponding 2-carboxy-derivatives 1a and 2a is reported, involving one-pot sequential Zn2+-assisted biomimetic oxidation Of L-dopa and L-cysteine, 5-S-cysteinyldopa or 2-S-cysteinyldopa. (C) 2009 Elsevier Ltd. All rights reserved.