[(S)-1-[1-((1R,6S)-6-Carbamoyl-cyclohex-2-enylcarbamoyl)-cyclohexylcarbamoyl]-2-(4-phosphonooxy-phenyl)-ethyl]-carbamic acid 3-amino-benzyl ester

• 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: [(S)-1-[1-((1R,6S)-6-Carbamoyl-cyclohex-2-enylcarbamoyl)-cyclohexylcarbamoyl]-2-(4-phosphonooxy-phenyl)-ethyl]-carbamic acid 3-amino-benzyl ester
• 英文别名: (3-aminophenyl)methyl N-[(2S)-1-[[1-[[(1R,6S)-6-carbamoylcyclohex-2-en-1-yl]carbamoyl]cyclohexyl]amino]-1-oxo-3-(4-phosphonooxyphenyl)propan-2-yl]carbamate
• 化学式: C₃₁H₄₀N₅O₉P
• 分子量: 657.66
• InChiKey: YENDXPUMHXTISG-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  232
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Fmoc-O-磷酸基-L-酪氨酸 、 3-N-((tert-butyloxy)carbonylamino)benzyl-4-nitrophenyl carbonate 、 1-(FMOC-氨基)环己羧酸 在 N-<(dimethylamino)-1H-1,2,3-triazolo<4,5-b>pyridin-1-ylmethylene>-N-methylmethanaminium hexaflurophosphate N-oxide 、 O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 生成 [(S)-1-[1-((1R,6S)-6-Carbamoyl-cyclohex-2-enylcarbamoyl)-cyclohexylcarbamoyl]-2-(4-phosphonooxy-phenyl)-ethyl]-carbamic acid 3-amino-benzyl ester 、 [(S)-1-[1-((1S,6R)-6-Carbamoyl-cyclohex-2-enylcarbamoyl)-cyclohexylcarbamoyl]-2-(4-phosphonooxy-phenyl)-ethyl]-carbamic acid 3-amino-benzyl ester
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and X-ray Crystallography of a High-Affinity Antagonist of the Grb2-SH2 Domain Containing an Asparagine Mimetic

  摘要：

  Previous efforts in the search for molecules capable of blocking the associations between the activated tyrosine kinase growth factor receptors and the SH2 domain of Grb2 had resulted in the identification of 3-amino-Z-pTyr-Ac(6)c-Asn-NH2, a high-affinity and selective antagonist of this SH2 domain. In the present paper, we report the successful replacement of asparagine in this compound by a beta-amino acid mimetic, which brings us closer to our objective of identifying a Grb2-SH2 antagonist suitable for pharmacological investigations.

  DOI：

  10.1021/jm991013u