(S)-5,5,5',5'-tetrafluoroleucine | 1002331-15-8

• 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: (S)-5,5,5',5'-tetrafluoroleucine
• 英文别名: (S)-2-amino-4-difluoromethyl-5,5-difluoro-pentanoic acid；(2S)-2-amino-4-(difluoromethyl)-5,5-difluoropentanoic acid
• CAS: 1002331-15-8
• 化学式: C₆H₉F₄NO₂
• 分子量: 203.137
• InChiKey: FEJFNCLJBAXECJ-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-5,5,5',5'-tetrafluoroleucine 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 以89%的产率得到(S)-2-(9-fluorenylmethoxycarbonylamino)-5,5-difluoro-4-difluoromethyl-pentanoic acid
  参考文献：
  名称：

  Chemoenzymatic Synthesis of (S)-Hexafluoroleucine and (S)-Tetrafluoroleucine

  摘要：

  We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5',5',5'-hexafluoroleucine (Hfl) and (S)-5,5,5',5'-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal center dot mol(-1) more favorable compared to Hfl.

  DOI：

  10.1021/ol702470j
• 作为产物：
  描述：

  在 ammonium hydroxide 、 甲酸铵 formate dehydrogenase 、 L-phenylalanine dehydrogenase 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 以46.1%的产率得到(S)-5,5,5',5'-tetrafluoroleucine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of (S)-Hexafluoroleucine and (S)-Tetrafluoroleucine

  摘要：

  We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5',5',5'-hexafluoroleucine (Hfl) and (S)-5,5,5',5'-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal center dot mol(-1) more favorable compared to Hfl.

  DOI：

  10.1021/ol702470j

文献信息

• Chemoenzymatic Synthesis of (<i>S</i>)-Hexafluoroleucine and (<i>S</i>)-Tetrafluoroleucine
  作者：Hsien-Po Chiu、Richard P. Cheng

  DOI：10.1021/ol702470j

  日期：2007.12.1

  We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5',5',5'-hexafluoroleucine (Hfl) and (S)-5,5,5',5'-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal center dot mol(-1) more favorable compared to Hfl.