N-<<2-<2-nitrophenyl)dithio>-1-phenylethoxy>carbonyl>glycine | 147529-19-9

• 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-<<2-<2-nitrophenyl)dithio>-1-phenylethoxy>carbonyl>glycine
• 英文别名: 2-[[2-[(2-Nitrophenyl)disulfanyl]-1-phenylethoxy]carbonylamino]acetic acid
• CAS: 147529-19-9
• 化学式: C₁₇H₁₆N₂O₆S₂
• 分子量: 408.456
• InChiKey: GGDGDOJPQIGERA-UHFFFAOYSA-N

物化性质

• 沸点：
  627.3±55.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甘氨酸苄酯盐酸盐 、 N-<<2-<2-nitrophenyl)dithio>-1-phenylethoxy>carbonyl>glycine 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以87%的产率得到N-<<2-<2-nitrophenyl)dithio>-1-phenylethoxy>carbonyl>glycylglycine benzyl ester
  参考文献：
  名称：

  An affinity chromatographic method for the purification of water-insoluble peptides

  摘要：

  A simple and efficient affinity chromatographic method is described for the purification of hydrophobic and/or protected synthetic peptides in organic solvent. This affinity method entails the use of a new protecting group that contains a UV-active disulfide moiety ([2-[(2-nitrophenyl)dithio]-1-phenylethoxy]carbonyl, NpSSPeoc). NpSSPeoc is electrophilic and can be immobilized by a thiolate-disulfide interchange reaction on a thiol-containing solid support. Alternatively, NpSSPeoc can be converted into a nucleophilic thiol ((2-mercapto-1-phenylethoxy)carbonyl, HSPeoc) and immobilized by an electrophilic solid support. NpSSPeoc can be quantified via an Ellman-type assay to measure the amount of full-length peptide at the completion of a solid-phase synthesis before and/or after cleavage from the synthesis resin. NpSSPeoc can be removed with 25% trifluoroacetic acid in methylene chloride. Four peptides incorporating NpSSPeoc at the N-terminus were synthesized. Affinity chromatography was performed on these peptides using 1 % cross-linked polystyrene supports which incorporate a mercury(II) trifluoroacetate, disulfide, alkyl thiol, or iodoacetamide functionality. The results indicate that the highest and most consistent yields of purified peptide are obtained using the combination of HSPeoc and a polystyrene support incorporating the iodoacetamide functionality.

  DOI：

  10.1021/jo00058a007
• 作为产物：
  描述：

  2-((2-methyl-2-propyl)thio)-1-phenylethyl phenyl carbonate 在 苄基三甲基氢氧化铵 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-<<2-<2-nitrophenyl)dithio>-1-phenylethoxy>carbonyl>glycine
  参考文献：
  名称：

  An affinity chromatographic method for the purification of water-insoluble peptides

  摘要：

  A simple and efficient affinity chromatographic method is described for the purification of hydrophobic and/or protected synthetic peptides in organic solvent. This affinity method entails the use of a new protecting group that contains a UV-active disulfide moiety ([2-[(2-nitrophenyl)dithio]-1-phenylethoxy]carbonyl, NpSSPeoc). NpSSPeoc is electrophilic and can be immobilized by a thiolate-disulfide interchange reaction on a thiol-containing solid support. Alternatively, NpSSPeoc can be converted into a nucleophilic thiol ((2-mercapto-1-phenylethoxy)carbonyl, HSPeoc) and immobilized by an electrophilic solid support. NpSSPeoc can be quantified via an Ellman-type assay to measure the amount of full-length peptide at the completion of a solid-phase synthesis before and/or after cleavage from the synthesis resin. NpSSPeoc can be removed with 25% trifluoroacetic acid in methylene chloride. Four peptides incorporating NpSSPeoc at the N-terminus were synthesized. Affinity chromatography was performed on these peptides using 1 % cross-linked polystyrene supports which incorporate a mercury(II) trifluoroacetate, disulfide, alkyl thiol, or iodoacetamide functionality. The results indicate that the highest and most consistent yields of purified peptide are obtained using the combination of HSPeoc and a polystyrene support incorporating the iodoacetamide functionality.

  DOI：

  10.1021/jo00058a007