benzyl (S)-2-(5-(dimethylamino)naphthalene-1-sulfonamidyl)-3-hydroxypropionate | 246048-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzyl (S)-2-(5-(dimethylamino)naphthalene-1-sulfonamidyl)-3-hydroxypropionate
• CAS: 246048-04-4
• 化学式: C₂₂H₂₄N₂O₅S
• 分子量: 428.509
• InChiKey: PPDAUGUHGXZSMP-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  95.94
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl (S)-2-(5-(dimethylamino)naphthalene-1-sulfonamidyl)-3-hydroxypropionate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 邻四氯苯醌 、 氢气 、 达卡巴嗪 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， -42.0~20.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 (2S)-3-[2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-3,4-dihydroxy-5-methoxybenzoyl]oxy-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]propanoic acid
  参考文献：
  名称：

  Probing the Role of Polyphenol Oxidation in Mediating Insect−Pathogen Interactions. Galloyl-Derived Electrophilic Traps for the Lymantria dispar Nuclear Polyhedrosis Virus Matrix Protein Polyhedrin

  摘要：

  Galloyl-derived orthoquinone probes have been designed, synthesized, and utilized in an ongoing study of insect-pathogen interactions. A stable galloyl-derived orthoquinone O-methyl ether modified with both acidic and fluorescent appendages was successful in trapping the model nucleophile cysteine, a test protein bearing a single cysteine residue, and the viral occlusion body matrix protein polyhedrin from Lymantria dispar nuclear polyhedrosis virus (LdNPV), a pathogen of the gypsy moth caterpillar (GMc). This latter observation may be related to the molecular mechanism by which gallotannins decrease LdNPV infectivity in GMc's. Sufficient site isolation was not achieved with a polymer-bound reactive galloyl hydroxyorthoquinone electrophile to permit similar nucleophile trapping to compete with oligomerization.

  DOI：

  10.1021/jo982477n
• 作为产物：
  描述：

  丹酰氯 、 L-丝氨酸苄酯盐酸盐 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 14.0h， 以88%的产率得到benzyl (S)-2-(5-(dimethylamino)naphthalene-1-sulfonamidyl)-3-hydroxypropionate
  参考文献：
  名称：

  Probing the Role of Polyphenol Oxidation in Mediating Insect−Pathogen Interactions. Galloyl-Derived Electrophilic Traps for the Lymantria dispar Nuclear Polyhedrosis Virus Matrix Protein Polyhedrin

  摘要：

  Galloyl-derived orthoquinone probes have been designed, synthesized, and utilized in an ongoing study of insect-pathogen interactions. A stable galloyl-derived orthoquinone O-methyl ether modified with both acidic and fluorescent appendages was successful in trapping the model nucleophile cysteine, a test protein bearing a single cysteine residue, and the viral occlusion body matrix protein polyhedrin from Lymantria dispar nuclear polyhedrosis virus (LdNPV), a pathogen of the gypsy moth caterpillar (GMc). This latter observation may be related to the molecular mechanism by which gallotannins decrease LdNPV infectivity in GMc's. Sufficient site isolation was not achieved with a polymer-bound reactive galloyl hydroxyorthoquinone electrophile to permit similar nucleophile trapping to compete with oligomerization.

  DOI：

  10.1021/jo982477n