Cbz-Asp(α-OBn)-Ser(OBn) | 359868-57-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: Cbz-Asp(α-OBn)-Ser(OBn)
• 英文别名: N(1)Ser-OBn.Cbz-Asp(1)-OBn；benzyl (2S)-4-[[(2S)-3-hydroxy-1-oxo-1-phenylmethoxypropan-2-yl]amino]-4-oxo-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 359868-57-8
• 化学式: C₂₉H₃₀N₂O₈
• 分子量: 534.566
• InChiKey: ZJYVLOWUWNZWBC-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Cbz-Asp(α-OBn)-Ser(OBn) 在 palladium on activated charcoal 伯吉斯试剂 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 1.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 (S)-2-((S)-2-Amino-2-carboxy-ethyl)-4,5-dihydro-oxazole-4-carboxylic acid
  参考文献：
  名称：

  A Rational Approach to the Design of Selective Substrates and Potent Nontransportable Inhibitors of the Excitatory Amino Acid Transporter EAAC1 (EAAT3). New Glutamate and Aspartate Analogues as Potential Neuroprotective Agents

  摘要：

  Two three-dimensional receptor interaction models for EAAT substrates and nontransportable inhibitors have been developed, and new glutamate (Glu) and aspartate (Asp) analogues have been synthesized. The analogues la and 3 represent novel lead compounds for the development of EAAT substrates and nontransportable inhibitors, selective for EAATs over iGluRs, as possible neuroprotective agents useful to minimize the progression of chronic or acute neurodegenerative diseases, The role played by the protonatable amine function in the interaction with EAATs has been discussed.

  DOI：

  10.1021/jm015509z
• 作为产物：
  描述：

  N-苄氧羰基-L-天冬氨酸 1-苄酯 、 L-丝氨酸苄酯盐酸盐 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以80%的产率得到Cbz-Asp(α-OBn)-Ser(OBn)
  参考文献：
  名称：

  A Rational Approach to the Design of Selective Substrates and Potent Nontransportable Inhibitors of the Excitatory Amino Acid Transporter EAAC1 (EAAT3). New Glutamate and Aspartate Analogues as Potential Neuroprotective Agents

  摘要：

  Two three-dimensional receptor interaction models for EAAT substrates and nontransportable inhibitors have been developed, and new glutamate (Glu) and aspartate (Asp) analogues have been synthesized. The analogues la and 3 represent novel lead compounds for the development of EAAT substrates and nontransportable inhibitors, selective for EAATs over iGluRs, as possible neuroprotective agents useful to minimize the progression of chronic or acute neurodegenerative diseases, The role played by the protonatable amine function in the interaction with EAATs has been discussed.

  DOI：

  10.1021/jm015509z

文献信息

• A Rational Approach to the Design of Selective Substrates and Potent Nontransportable Inhibitors of the Excitatory Amino Acid Transporter EAAC1 (EAAT3). New Glutamate and Aspartate Analogues as Potential Neuroprotective Agents
  作者：Giuseppe Campiani、Meri De Angelis、Silvia Armaroli、Caterina Fattorusso、Bruno Catalanotti、Anna Ramunno、Vito Nacci、Ettore Novellino、Christof Grewer、Diana Ionescu、Thomas Rauen、Roger Griffiths、Colin Sinclair、Elena Fumagalli、Tiziana Mennini

  DOI：10.1021/jm015509z

  日期：2001.8.1

  Two three-dimensional receptor interaction models for EAAT substrates and nontransportable inhibitors have been developed, and new glutamate (Glu) and aspartate (Asp) analogues have been synthesized. The analogues la and 3 represent novel lead compounds for the development of EAAT substrates and nontransportable inhibitors, selective for EAATs over iGluRs, as possible neuroprotective agents useful to minimize the progression of chronic or acute neurodegenerative diseases, The role played by the protonatable amine function in the interaction with EAATs has been discussed.