Fmoc-2S,4S-perfluoro-tert-butyl-hydroxyproline | 1610605-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-2S,4S-perfluoro-tert-butyl-hydroxyproline
• 英文别名: Fmoc-(2S,4S)-perfluoro-tert-butyl-4-hydroxyproline；N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-(nonafluoro-t-butyl)-cis-L-hydroxyproline；(2S,4S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl]oxypyrrolidine-2-carboxylic acid
• CAS: 1610605-22-5
• 化学式: C₂₄H₁₈F₉NO₅
• 分子量: 571.396
• InChiKey: LFRRTLDHTYUNNO-SGTLLEGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  Boc-2S,4S-perfluoro-tert-butyl-hydroxyproline methyl ester 在 盐酸 、 水 、 potassium carbonate 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 34.0h， 生成 Fmoc-2S,4S-perfluoro-tert-butyl-hydroxyproline
  参考文献：
  名称：

  (2S,4R)- and (2S,4S)-Perfluoro-tert-butyl 4-Hydroxyproline: Two Conformationally Distinct Proline Amino Acids for Sensitive Application in ¹⁹F NMR

  摘要：

  (2S,4R)- and (2S,4S)-perfluoro-tert-butyl 4-hydroxyproline were synthesized (as Fmoc-, Boc-, and free amino acids) in 2-5 steps. The key step of each synthesis was a Mitsunobu reaction with perfluoro-tert-butanol, which incorporated a perfluoro-tert-butyl group, with nine chemically equivalent fluorines. Both amino acids were incorporated in model α-helical and polyproline helix peptides. Each amino acid exhibited distinct conformational preferences, with (2S,4R)-perfluoro-tert-butyl 4-hydroxyproline promoting polyproline helix. Peptides containing these amino acids were sensitively detected by (19)F NMR, suggesting their use in probes and medicinal chemistry.

  DOI：

  10.1021/jo5008674

文献信息

• [EN] PERFLUORO-TERT-BUTYL HYDROXYPROLINE<br/>[FR] PERFLUORO-TERT-BUTYLE HYDROXYPROLINE
  申请人：ZONDLO NEAL

  公开号：WO2014127052A1

  公开（公告）日：2014-08-21

  The present invention provides novel analogues of alpha amino acids, comprising a perfluoro-tert-butyl group, and molecules comprising the novel analogues. Also provided are a wide range of applications of the novel analogues in therapeutics, theranostics and pharmaceuticals as well as in imaging applications. In particular, the use of the novel analogues in detecting or modifying a target molecule is provided.

  本发明提供了新型α氨基酸的类似物，包括全氟叔丁基基团，以及包含这些新型类似物的分子。还提供了这些新型类似物在治疗学、治疗诊断学、制药学以及成像应用中的广泛应用。特别提供了在检测或修改靶分子中使用这些新型类似物的方法。
• PERFLUORO-TERT-BUTYL HYDROXYPROLINE
  申请人：ZONDLO Neal

  公开号：US20160002159A1

  公开（公告）日：2016-01-07

  The present invention provides novel analogues of alpha amino acids, comprising a perfluoro-tert-butyl group, and molecules comprising the novel analogues. Also provided are a wide range of applications of the novel analogues in therapeutics, theranostics and pharmaceuticals as well as in imaging applications. In particular, the use of the novel analogues in detecting or modifying a target molecule is provided.

  本发明提供了新型的α-氨基酸类似物，包括全氟叔丁基基团，以及包含这些新型类似物的分子。此外，本发明还提供了广泛的应用，包括在治疗、治疗诊断和制药以及成像应用中使用这些新型类似物。特别地，本发明提供了在检测或修改目标分子中使用这些新型类似物的用途。
• (2<i>S</i>,4<i>R</i>)- and (2<i>S</i>,4<i>S</i>)-Perfluoro-<i>tert</i>-butyl 4-Hydroxyproline: Two Conformationally Distinct Proline Amino Acids for Sensitive Application in ¹⁹F NMR
  作者：Caitlin M. Tressler、Neal J. Zondlo

  DOI：10.1021/jo5008674

  日期：2014.6.20

  (2S,4R)- and (2S,4S)-perfluoro-tert-butyl 4-hydroxyproline were synthesized (as Fmoc-, Boc-, and free amino acids) in 2-5 steps. The key step of each synthesis was a Mitsunobu reaction with perfluoro-tert-butanol, which incorporated a perfluoro-tert-butyl group, with nine chemically equivalent fluorines. Both amino acids were incorporated in model α-helical and polyproline helix peptides. Each amino acid exhibited distinct conformational preferences, with (2S,4R)-perfluoro-tert-butyl 4-hydroxyproline promoting polyproline helix. Peptides containing these amino acids were sensitively detected by (19)F NMR, suggesting their use in probes and medicinal chemistry.