N^α-benzyloxycarbonyl-N^G-biphenyl-4-sulphonyl-L-arginine | 162611-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N^α-benzyloxycarbonyl-N^G-biphenyl-4-sulphonyl-L-arginine
• 英文别名: (2S)-5-[[amino-[(4-phenylphenyl)sulfonylamino]methylidene]amino]-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 162611-59-8
• 化学式: C₂₆H₂₈N₄O₆S
• 分子量: 524.598
• InChiKey: XVBHAWVVRBGIGX-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N^α-benzyloxycarbonyl-N^G-biphenyl-4-sulphonyl-L-arginine 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以83%的产率得到N^G-biphenyl-4-sulphonyl-L-arginine
  参考文献：
  名称：

  Two new Protecting Groups for the Guanidino Function of arginine

  摘要：

  Two new synthons, Fmoc-L-Arg(biphenyl-4-sulphonyl)-OH (8) and Fmoc-Arg(4-methoxy-3-t-butylbenzenesulphonyl)-OH (14), are prepared for the synthesis of arginine-containing peptides. These groups are cleaved by commonly employed trifluoroacetic acid and methanesulphonic acid. Kinetic studies reveal that extended bicyclic aromatic conjugation, as in biphenyl, slightly improves the acid lability compared to the electron-donating t-butyl group.

  DOI：

  10.1002/prac.19953370103
• 作为产物：
  描述：

  氯甲酸苄酯 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 N^α-benzyloxycarbonyl-N^G-biphenyl-4-sulphonyl-L-arginine
  参考文献：
  名称：

  Two new Protecting Groups for the Guanidino Function of arginine

  摘要：

  Two new synthons, Fmoc-L-Arg(biphenyl-4-sulphonyl)-OH (8) and Fmoc-Arg(4-methoxy-3-t-butylbenzenesulphonyl)-OH (14), are prepared for the synthesis of arginine-containing peptides. These groups are cleaved by commonly employed trifluoroacetic acid and methanesulphonic acid. Kinetic studies reveal that extended bicyclic aromatic conjugation, as in biphenyl, slightly improves the acid lability compared to the electron-donating t-butyl group.

  DOI：

  10.1002/prac.19953370103

文献信息

• Two new Protecting Groups for the Guanidino Function of arginine
  作者：Syed Safdar Ali、Khalid Mohammed Khan、Hartmut Echner、Wolfgang Voelter、Mashooda Hasan、Atta-ur-Rahman

  DOI：10.1002/prac.19953370103

  日期：——

  Two new synthons, Fmoc-L-Arg(biphenyl-4-sulphonyl)-OH (8) and Fmoc-Arg(4-methoxy-3-t-butylbenzenesulphonyl)-OH (14), are prepared for the synthesis of arginine-containing peptides. These groups are cleaved by commonly employed trifluoroacetic acid and methanesulphonic acid. Kinetic studies reveal that extended bicyclic aromatic conjugation, as in biphenyl, slightly improves the acid lability compared to the electron-donating t-butyl group.