(S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-pentanedioic acid 5-benzyl ester | 205236-27-7

• 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: (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-pentanedioic acid 5-benzyl ester
• 英文别名: Ac-Tyr(PO3Bn2)-Glu(OBn)(OBn)-OH；(2S)-2-[[(2S)-2-acetamido-3-[4-bis(phenylmethoxy)phosphoryloxyphenyl]propanoyl]amino]-5-oxo-5-phenylmethoxypentanoic acid
• CAS: 205236-27-7
• 化学式: C₃₇H₃₉N₂O₁₀P
• 分子量: 702.698
• InChiKey: XSRHTMROBSJJTL-HEVIKAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  167
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-pentanedioic acid 5-benzyl ester 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 2.58h， 生成 (S)-4-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-4-[(6-hydroxy-hexyl)-methyl-carbamoyl]-butyric acid benzyl ester
  参考文献：
  名称：

  Potent Dipeptide Inhibitors of the pp60^c-src SH2 Domain

  摘要：

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.

  DOI：

  10.1021/jm970853a
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-苄酯 在 吡啶 、 盐酸 、 二乙基异丙基胺 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 氟化氢吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 55.0h， 生成 (S)-2-{(S)-2-Acetylamino-3-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-propionylamino}-pentanedioic acid 5-benzyl ester
  参考文献：
  名称：

  Potent Dipeptide Inhibitors of the pp60^c-src SH2 Domain

  摘要：

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.

  DOI：

  10.1021/jm970853a

文献信息

• Potent Dipeptide Inhibitors of the pp60<i>^c</i><i>^-</i><i>^src</i> SH2 Domain
  作者：Gregory J. Pacofsky、Karen Lackey、Krystal J. Alligood、Judd Berman、Paul S. Charifson、Renae M. Crosby、George F. Dorsey,、Paul L. Feldman、Tona M. Gilmer、Conrad W. Hummel、Steven R. Jordan、Christopher Mohr、Lisa M. Shewchuk、Daniel D. Sternbach、Marc Rodriguez

  DOI：10.1021/jm970853a

  日期：1998.5.1

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.