(2R,6S)-2,6-Diamino-4-methylene-heptanedioic acid | 100910-34-7

• 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
• 英文名称: (2R,6S)-2,6-Diamino-4-methylene-heptanedioic acid
• 英文别名: (2S,6R)-2,6-diamino-4-methylideneheptanedioic acid
• CAS: 100910-34-7
• 化学式: C₈H₁₄N₂O₄
• 分子量: 202.21
• InChiKey: XHOSYVGVHNEHGK-OLQVQODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Triethyl 1-(formylamino)-5-(methanesulfonyloxy)-3-methylene-1,1,5-pentane tricarboxylate 在 Lindlar's catalyst 盐酸 、 sodium hydroxide 、 sodium azide 、 氢气 、 三乙胺 、 sodium chloride 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.75h， 生成 (2R,6S)-2,6-Diamino-4-methylene-heptanedioic acid
  参考文献：
  名称：

  The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?

  摘要：

  Unsaturated analogues of diaminopimelic acid have been synthesized. The amino acids were designed so that they would be reversible or irreversible inhibitors of both of the two last enzymes of the lysine pathway. The compounds were tested with meso-diaminopimelate decarboxylase. trans-3,4-Didehydrodiaminopimelic acid (2) was found to be the most potent inhibitor. The antibacterial activities did not correlate with enzyme inhibiting activities. 4-Methylenediaminopimelic acid 4 showed strong antibacterial properties. It is suggested that L,L-diaminopimelate epimerase could be the target enzyme.

  DOI：

  10.1021/jm00156a021

文献信息

• The lysine pathway as a target for a new genera of synthetic antibacterial antibiotics?
  作者：Jean Marc Girodeau、Constantin Agouridas、Maryse Masson、Roland Pineau、Francois Le Goffic

  DOI：10.1021/jm00156a021

  日期：1986.6

  Unsaturated analogues of diaminopimelic acid have been synthesized. The amino acids were designed so that they would be reversible or irreversible inhibitors of both of the two last enzymes of the lysine pathway. The compounds were tested with meso-diaminopimelate decarboxylase. trans-3,4-Didehydrodiaminopimelic acid (2) was found to be the most potent inhibitor. The antibacterial activities did not correlate with enzyme inhibiting activities. 4-Methylenediaminopimelic acid 4 showed strong antibacterial properties. It is suggested that L,L-diaminopimelate epimerase could be the target enzyme.