methyl (3R,4S,5R)-3-azido-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate | 245054-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3R,4S,5R)-3-azido-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate
• 英文别名: methyl (2S,3S,4aR,5R,8aR)-5-azido-2,3-dimethoxy-2,3-dimethyl-4a,5,8,8a-tetrahydro-1,4-benzodioxine-7-carboxylate
• CAS: 245054-39-1
• 化学式: C₁₄H₂₁N₃O₆
• 分子量: 327.337
• InChiKey: LBYFMMGIJADGOJ-AFCCXKIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (3R,4S,5R)-3-azido-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate 在 4-二甲氨基吡啶 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 6.0h， 生成 methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate
  参考文献：
  名称：

  奎尼酸向sh草酸衍生物的有效转化

  摘要：

  （-）- sh草酸甲酯和（-）-3-表-shi草酸酯和3-氨基shi草酸酯衍生物的合成已经通过短而有效的途径由奎宁酸实现。

  DOI：

  10.1016/s0040-4020(99)00431-7
• 作为产物：
  描述：

  (2S,3S,4aR,6S,8R,8aR)-八氢-6,8-二羟基-2,3-二甲氧基-2,3-二甲基-1,4-苯并二氧杂环己-6-羧酸甲酯 在 迭氮酸 、 草酰氯 、 偶氮二甲酸二异丙酯 、 二异丁基氢化铝 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 生成 methyl (3R,4S,5R)-3-azido-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate
  参考文献：
  名称：

  奎尼酸向sh草酸衍生物的有效转化

  摘要：

  （-）- sh草酸甲酯和（-）-3-表-shi草酸酯和3-氨基shi草酸酯衍生物的合成已经通过短而有效的途径由奎宁酸实现。

  DOI：

  10.1016/s0040-4020(99)00431-7

文献信息

• Mycobacterium tuberculosis Shikimate Kinase Inhibitors: Design and Simulation Studies of the Catalytic Turnover
  作者：Beatriz Blanco、Verónica Prado、Emilio Lence、José M. Otero、Carmela Garcia-Doval、Mark J. van Raaij、Antonio L. Llamas-Saiz、Heather Lamb、Alastair R. Hawkins、Concepción González-Bello

  DOI：10.1021/ja405853p

  日期：2013.8.21

  Shikimate kinase (SK) is an essential enzyme in several pathogenic bacteria and does not have any counterpart in human cells, thus making it an attractive target for the development of new antibiotics. The key interactions of the substrate and product binding and the enzyme movements that are essential for catalytic turnover of the Mycobacterium tuberculosis shikimate kinase enzyme (Mt-SK) have been investigated by structural and computational studies. Based on these studies several substrate analogs were designed and assayed. The crystal structure of Mt-SK in complex with ADP and one of the most potent inhibitors has been solved at 2.15 angstrom. These studies reveal that the fixation of the diaxial conformation of the C4 and C5 hydroxyl groups recognized by the enzyme or the replacement of the C3 hydroxyl group in the natural substrate by an amino group is a promising strategy for inhibition because it causes a dramatic reduction of the flexibility of the LID and shikimic acid binding domains. Molecular dynamics simulation studies showed that the product is expelled from the active site by three arginines (Arg117, Arg136, and Arg58). This finding represents a previously unknown key role of these conserved residues. These studies highlight the key role of the shikimic acid binding domain in the catalysis and provide guidance for future inhibitor designs.
• An efficient transformation of quinic acid to shikimic acid derivatives
  作者：Cristina Alves、M.Teresa Barros、Christopher D. Maycock、M.Rita Ventura

  DOI：10.1016/s0040-4020(99)00431-7

  日期：1999.7

  The synthesis of (−)-methyl shikimate and (−)-methyl 3-epi-shikimate and the 3-aminoshikimate derivative have been achieved via short and efficient routes from quinic acid.

  （-）- sh草酸甲酯和（-）-3-表-shi草酸酯和3-氨基shi草酸酯衍生物的合成已经通过短而有效的途径由奎宁酸实现。