2-(1-carboxyethylcarbamoyl)pyrrolidine-1-carboxylic acid 1-(9H-fluoren-9-ylmethyl) ester | 144575-15-5

• 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: 2-(1-carboxyethylcarbamoyl)pyrrolidine-1-carboxylic acid 1-(9H-fluoren-9-ylmethyl) ester
• 英文别名: Fmoc-Pro-Ala-OH；(S)-2-((S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)pyrrolidine-2-carboxamido)propanoic acid；(2S)-2-[[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]amino]propanoic acid
• CAS: 144575-15-5
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: IBWBVBRWVISRRH-XOBRGWDASA-N

物化性质

• 沸点：
  679.2±55.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-carboxyethylcarbamoyl)pyrrolidine-1-carboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 在 1-羟基苯并三唑 、 苯甲醚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-{1-[4-(2-(4-[1-(1-benzhydryloxycarbonyl-2-phenylethylcarbamoyl)ethylcarbamoyl]but-1-ynyl)phenyl)but-3-ynylcarbamoyl]ethylcarbamoyl}pyrrolidine-1-carboxylic acid 2H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Design and synthesis of a novel enediynyl pentapeptide with predominantly β-turn structural motif and its potential as a fluorescence-based chemosensor

  摘要：

  A novel enediynyl pentapeptide in the protected form 1 was synthesized and characterized. It exists predominantly in beta-turn structural motif as revealed by variable temperature NMR and CD spectroscopy. In the presence of transition metal ions and gold nanoparticles, the fluorescence intensity of the peptide got enhanced with remarkable quantum yield with the Z-enediynyl omega-amino acid acting as a fluorophoric reporter. The interesting photophysical behaviors with alkali and alkaline earth metal ions are also reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.038
• 作为产物：
  描述：

  2-(1-(benzhydryloxycarbonyl)ethylcarbamoyl)pyrrolidine-1-carboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2-(1-carboxyethylcarbamoyl)pyrrolidine-1-carboxylic acid 1-(9H-fluoren-9-ylmethyl) ester
  参考文献：
  名称：

  Design and synthesis of a novel enediynyl pentapeptide with predominantly β-turn structural motif and its potential as a fluorescence-based chemosensor

  摘要：

  A novel enediynyl pentapeptide in the protected form 1 was synthesized and characterized. It exists predominantly in beta-turn structural motif as revealed by variable temperature NMR and CD spectroscopy. In the presence of transition metal ions and gold nanoparticles, the fluorescence intensity of the peptide got enhanced with remarkable quantum yield with the Z-enediynyl omega-amino acid acting as a fluorophoric reporter. The interesting photophysical behaviors with alkali and alkaline earth metal ions are also reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.038

文献信息

• New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: application of peptide coupling agents EDC and HBTU
  作者：Vommina V. Sureshbabu、H. S. Lalithamba、N. Narendra、H. P. Hemantha

  DOI：10.1039/b920290k

  日期：——

  Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved.

  使用肽偶联剂，EDC和 HBTU描述。该程序高效，实用并且适用于多种羧酸，包括ñ保护的氨基酸。使用相同的试剂，还可以从酸一锅合成尿素，二肽基脲酯和氨基甲酸酯。
• Mixed-Phase Synthesis of Glycopeptides Using a <i>N</i>-Peptidyl-2,4-dinitrobenzenesulfonamide–Thioacid Ligation Strategy
  作者：Partha Karmakar、Rommel S. Talan、Steven J. Sucheck

  DOI：10.1021/ol202163e

  日期：2011.10.7

  A strategy for the solid phase peptide synthesis (SPPS) and coupling of N-peptidyl and N-glycopeptidyl 2,4-dinitrobenzenesulfonamides (dNBS) with C-terminal peptidyl thioacids has been developed. The resulting N-dDNBS peptides were coupled to generate longer peptides. Ligation reactions were complete within 15 to 20 min.

  已经开发了固相肽合成 (SPPS) 和N-肽基和N-糖肽基 2,4-二硝基苯磺酰胺(dNBS) 与 C 端肽基硫代酸的偶联策略。将所得的N- dDNBS 肽偶联以产生更长的肽。连接反应在 15 到 20 分钟内完成。
• US5439806A
  申请人：——

  公开号：US5439806A

  公开（公告）日：1995-08-08
• US5639859A
  申请人：——

  公开号：US5639859A

  公开（公告）日：1997-06-17