Fmoc-Orn(Boc) p-nitrobenzyl ester | 134653-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Orn(Boc) p-nitrobenzyl ester
• 英文别名: (4-nitrophenyl)methyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 134653-29-5
• 化学式: C₃₂H₃₅N₃O₈
• 分子量: 589.645
• InChiKey: OVQGZRRIMDPSMM-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  146.1
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Orn(Boc) p-nitrobenzyl ester 在 哌啶 、 碳酸氢钠 、 三氟乙酸 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (S)-2-Amino-5-(bis-benzyloxycarbonylmethyl-amino)-pentanoic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Synthesis of peptides containing unnatural, metal-ligating residues: aminodiacetic acid as a peptide side chain

  摘要：

  Peptides possessing a pair of residues separated by one turn in the alpha-helical conformation and potentially capable of ligating a single metal ion in aqueous solution were designed. It was predicted that the resulting cross-link would shift toward alpha-helix the random coil/alpha-helix equilibrium. The syntheses of 10 peptides Ac-Ada(l)Ala(m)Ada(l)(Ala4GluLys)n-NH2 where Ada(l) is an L-alpha-amino acid residue with an aminodiacetic acid bearing side chain, -(CH2)(l)N(CH2CO2H)2 (with values of l, m, and n as follows: 1, 2, 3 (1); 1, 3, 1 (2a); 1, 3, 2 (2b); 1, 3, 3 (2c); 2, 2, 3 (3); 2, 3, 3 (4); 3, 2, 3 (5); 3, 3, 3 (6); 4, 2, 3 (7); 4, 3, 3 (8)) are described using Boc chemistry on p-methylbenzhydrylamine resin. The aminodiacetic acid bearing residues were incorporated with side chains protected as the dibenzyl esters. To avoid side reactions, residues Ada(l) for l = 1 and 2 were incorporated by a block approach. Peptide structures were confirmed by observation of the predicted parent ions in the FAB MS. The circular dichroism spectra of several of these peptides that posses a pair of metal-ligating residues separated by two or three intervening residues have previously been shown to undergo changes on addition of metal ions consistent with appreciable enhancement of helix content.

  DOI：

  10.1021/jo00014a006
• 作为产物：
  描述：

  1-(氯甲基)-4-硝基苯 、 N-Fmoc-N'-Boc-L-鸟氨酸 在 碳酸氢钠 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到Fmoc-Orn(Boc) p-nitrobenzyl ester
  参考文献：
  名称：

  Synthesis of peptides containing unnatural, metal-ligating residues: aminodiacetic acid as a peptide side chain

  摘要：

  Peptides possessing a pair of residues separated by one turn in the alpha-helical conformation and potentially capable of ligating a single metal ion in aqueous solution were designed. It was predicted that the resulting cross-link would shift toward alpha-helix the random coil/alpha-helix equilibrium. The syntheses of 10 peptides Ac-Ada(l)Ala(m)Ada(l)(Ala4GluLys)n-NH2 where Ada(l) is an L-alpha-amino acid residue with an aminodiacetic acid bearing side chain, -(CH2)(l)N(CH2CO2H)2 (with values of l, m, and n as follows: 1, 2, 3 (1); 1, 3, 1 (2a); 1, 3, 2 (2b); 1, 3, 3 (2c); 2, 2, 3 (3); 2, 3, 3 (4); 3, 2, 3 (5); 3, 3, 3 (6); 4, 2, 3 (7); 4, 3, 3 (8)) are described using Boc chemistry on p-methylbenzhydrylamine resin. The aminodiacetic acid bearing residues were incorporated with side chains protected as the dibenzyl esters. To avoid side reactions, residues Ada(l) for l = 1 and 2 were incorporated by a block approach. Peptide structures were confirmed by observation of the predicted parent ions in the FAB MS. The circular dichroism spectra of several of these peptides that posses a pair of metal-ligating residues separated by two or three intervening residues have previously been shown to undergo changes on addition of metal ions consistent with appreciable enhancement of helix content.

  DOI：

  10.1021/jo00014a006