N,N'-ethylenedicarbonyl-bis[(S)-3-(1-naphthyl)alanyl-(S)-2-phenylglycine tert-butyl ester]

• 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: N,N'-ethylenedicarbonyl-bis[(S)-3-(1-naphthyl)alanyl-(S)-2-phenylglycine tert-butyl ester]
• 英文别名: tert-butyl (2S)-2-[[(2S)-2-[[4-[[(2S)-1-[[(1S)-2-[(2-methylpropan-2-yl)oxy]-2-oxo-1-phenylethyl]amino]-3-naphthalen-1-yl-1-oxopropan-2-yl]amino]-4-oxobutanoyl]amino]-3-naphthalen-1-ylpropanoyl]amino]-2-phenylacetate
• 化学式: C₅₄H₅₈N₄O₈
• 分子量: 891.077
• InChiKey: PTGMRQJPPMUETK-BYMVZKLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  66
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Cbz-3-(1-萘)-l-ala 在 吡啶 、 N-羟基丁二酰亚胺 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 123.0h， 生成 N,N'-ethylenedicarbonyl-bis[(S)-3-(1-naphthyl)alanyl-(S)-2-phenylglycine tert-butyl ester]
  参考文献：
  名称：

  Enantioselective Fluorescence Recognition of Chiral Amines by N-Acyl-(S)-1-naphthylalanyl-(S)-phenylglycine and N-Acyl-(S)-1-naphthylalanyl-(S)-1-naphthylalanine Dipeptides Bridged by a 1,2-Phenylene or an Ethylene Spacer Chain

  摘要：

  This study sought to support the development of enantioselective dipeptide fluorescence sensors by examining the ability of the N-acyl-(S)-1-naphthylalanyl-(S)-phenylglycine and N-acyl-(S)-1-naphthylalanyl-(S)-1naphthylalanine dipeptides (bridged by the 1,2-phenylene or ethylene spacer chain) to discriminate between aliphatic amine-derived (S)- and (R)-enantiomer s. The results indicated that both hydrogen-bonding interactions in the ground state and charge-transfer interactions in the excited state are involved in the fluorescence quenching of these bridged dipeptides by chiral amines to produce the upward curving Stern Volmer plots. In addition, the numerical analysis of these plots led to the conclusion that the bridged naphthylalanylphenylglycine dipeptide shows the highest ability to differentiate the (S)-enantiomer from (R)-enantiomer when the emission of this dipeptide is quenched by chiral alaninols.

  DOI：

  10.3987/com-13-12694

文献信息

• Enantioselective Fluorescence Recognition of Chiral Amines by N-Acyl-(S)-1-naphthylalanyl-(S)-phenylglycine and N-Acyl-(S)-1-naphthylalanyl-(S)-1-naphthylalanine Dipeptides Bridged by a 1,2-Phenylene or an Ethylene Spacer Chain
  作者：Tadamitsu Sakurai、Tomoe Ishikawa、Miho Sonobe、Akinori Hayakawa、Tetsutaro Igarashi

  DOI：10.3987/com-13-12694

  日期：——

  This study sought to support the development of enantioselective dipeptide fluorescence sensors by examining the ability of the N-acyl-(S)-1-naphthylalanyl-(S)-phenylglycine and N-acyl-(S)-1-naphthylalanyl-(S)-1naphthylalanine dipeptides (bridged by the 1,2-phenylene or ethylene spacer chain) to discriminate between aliphatic amine-derived (S)- and (R)-enantiomer s. The results indicated that both hydrogen-bonding interactions in the ground state and charge-transfer interactions in the excited state are involved in the fluorescence quenching of these bridged dipeptides by chiral amines to produce the upward curving Stern Volmer plots. In addition, the numerical analysis of these plots led to the conclusion that the bridged naphthylalanylphenylglycine dipeptide shows the highest ability to differentiate the (S)-enantiomer from (R)-enantiomer when the emission of this dipeptide is quenched by chiral alaninols.