1-甲氧基-3-吲哚基甲基硫代葡萄糖苷 | 5187-84-8

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-甲氧基-3-吲哚基甲基硫代葡萄糖苷
• 英文名称: 1-methoxy-3-indolylmethyl glucosinolate
• 英文别名: N-methoxy-3-indolylmethyl-glucosinolate；neoglucobrassicin；DS-glucohesperin；Neoglucobrassin (N-Methoxy-glucobrassin)；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(1-methoxyindol-3-yl)-N-sulfooxyethanimidothioate
• CAS: 5187-84-8
• 化学式: C₁₇H₂₂N₂O₁₀S₂
• 分子量: 478.501
• InChiKey: PKKMITFKYRCCOL-CMZRPVNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  214
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-甲氧基-3-吲哚基甲基硫代葡萄糖苷 在 葡糖硫苷酶(-20℃) 、 pH 7 phosphate buffer 作用下， 生成 (1-甲氧基吲哚-3-基)甲醇 、 3,3’-bis(1-methoxyindolyl)methane 、 甲基[(1-甲氧基-1H-吲哚-3-基)甲基]二硫代氨基甲酸酯 、 Caulilexin C; 1-甲氧基-3-吲哚乙腈 、
  参考文献：
  名称：

  Initial and Final Products, Nitriles, and Ascorbigens Produced in Myrosinase-Catalyzed Hydrolysis of Indole Glucosinolates

  摘要：

  Micellar electrokinetic capillary chromatography (MECC) was used to follow the myrosinase (beta-thioglucoside glucohydrolase EC 3.2.3.1)-catalyzed transformation of glucobrassicin (indol-3-ylmethylglucosinolate, 1a) and neoglucobrassicin (N-methoxyglucobrassicin, 1b) into nitriles, ascorbigens, and other products. The influence of pH, ascorbic acid, and Fe(II) ions was investigated. In the presence of ascorbic acid, (5 mM), thiocyanate ion and ascorbigens were the dominating products from 1a and 1b. In the presence of Fe(II) ions (2.5 mM), nitriles were the dominating products between pH 4 and 6-7. During hydrolysis of 1b in neutral or weakly basic solution, an unstable intermediate was detected by MECC. Comparisons of the rate of ascorbigen formation from 1a, 1b, and indol-3-ylcarbinol showed that ascorbigens were formed directly from ascorbate and unstable products of the hydrolysis of indole glucosinolates and that indol-3-ylcarbinols were not important intermediates. Structures of 1a, 1b, and products of 1b were confirmed by H-1 NMR, MS, and UV spectroscopy.

  DOI：

  10.1021/jf9708498