methyl (S)-2-((S)-2-((S)-2-((S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoyl)-2'-oxo-2,4-dihydro-1H-spiro[isoquinoline-3,3'-pyrrolidin]-1'-yl)propanamido)-5-((E)-2-nitroguanidino)pentanoate | 1191929-84-6

• 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: methyl (S)-2-((S)-2-((S)-2-((S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoyl)-2'-oxo-2,4-dihydro-1H-spiro[isoquinoline-3,3'-pyrrolidin]-1'-yl)propanamido)-5-((E)-2-nitroguanidino)pentanoate
• 英文别名: methyl (2S)-2-[[(2S)-2-[(3S)-2-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]-2'-oxospiro[1,4-dihydroisoquinoline-3,3'-pyrrolidine]-1'-yl]propanoyl]amino]-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoate
• CAS: 1191929-84-6
• 化学式: C₃₇H₅₀N₈O₁₀
• 分子量: 766.852
• InChiKey: YYVPILWBCYGMOF-DWMOVPQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  240
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-((S)-2-((S)-2-((S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoyl)-2'-oxo-2,4-dihydro-1H-spiro[isoquinoline-3,3'-pyrrolidin]-1'-yl)propanamido)-5-((E)-2-nitroguanidino)pentanoate 、 甲胺 以 乙醇 为溶剂， 反应 12.0h， 以94%的产率得到tert-butyl (S)-3-(benzyloxy)-1-((S)-1'-((S)-1-((S)-1-(methylamino)-5-((E)-2-nitroguanidino)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)-2'-oxo-1H-spiro[isoquinoline-3,3'-pyrrolidin]-2(4H)-yl)-1-oxopropan-2-ylcarbamate
  参考文献：
  名称：

  Tetrahydroisoquinoline-Based Spirocyclic Lactam as a Type II′ β-Turn Inducing Peptide Mimetic

  摘要：

  We present here spirocyclic lactam derivatives, embodying D-Phe and L-Ala amino acids as the central core and acting as tetrapeptide and hexapeptide mimetics. An efficient route for their synthesis is demonstrated by using the strategic combination of Seebach's self-reproduction of chirality chemistry and the Pictet-Spengler condensation as key steps. The conformational behavior of peptide mimetics was Investigated by Molecular modeling, X-ray crystallography, NMR (solvent and temperature dependence), IR spectroscopy, and circular dichroism. All data suggest very stable and highly predictable type II' beta-turn conformations.

  DOI：

  10.1021/jo901480d
• 作为产物：
  描述：

  (S)-2-((S)-2-((S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)-propanoyl)-2'-oxo-2,4-dihydro-1H-spiro[isoquinoline-3,3'-pyrrolidin]-1'-yl)propanoic acid 、 N_ω-nitro-L-arginine methyl ester hydrochloride 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以45%的产率得到methyl (S)-2-((S)-2-((S)-2-((S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoyl)-2'-oxo-2,4-dihydro-1H-spiro[isoquinoline-3,3'-pyrrolidin]-1'-yl)propanamido)-5-((E)-2-nitroguanidino)pentanoate
  参考文献：
  名称：

  Tetrahydroisoquinoline-Based Spirocyclic Lactam as a Type II′ β-Turn Inducing Peptide Mimetic

  摘要：

  We present here spirocyclic lactam derivatives, embodying D-Phe and L-Ala amino acids as the central core and acting as tetrapeptide and hexapeptide mimetics. An efficient route for their synthesis is demonstrated by using the strategic combination of Seebach's self-reproduction of chirality chemistry and the Pictet-Spengler condensation as key steps. The conformational behavior of peptide mimetics was Investigated by Molecular modeling, X-ray crystallography, NMR (solvent and temperature dependence), IR spectroscopy, and circular dichroism. All data suggest very stable and highly predictable type II' beta-turn conformations.

  DOI：

  10.1021/jo901480d