FMOC-Thr(t-Bu)-F | 130858-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: FMOC-Thr(t-Bu)-F
• 英文别名: N-(9-Fluorenylmethoxycarbonyl)-O-(t-Butyl)threonine Fluoride；9H-fluoren-9-ylmethyl N-[(2S,3R)-1-fluoro-3-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]carbamate
• CAS: 130858-99-0
• 化学式: C₂₃H₂₆FNO₄
• 分子量: 399.462
• InChiKey: PBUJDFBHIUBUMU-VLIAUNLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2,2-dimethyltetrahydrothiazole-4-carboxylic acid hydrochloride 、 FMOC-Thr(t-Bu)-F 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以8%的产率得到(R)-3-(N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyl)-L-threonyl)-2,2-dimethylthiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Rescuing Biological Activity from Synthetic Phakellistatin 19

  摘要：

  Phakellistatins is one of the families of Pro-rich cyclic peptides whose synthetic counterparts have revealed cytotoxicities that differ greatly from those displayed by their corresponding natural ones. This is also the case of the last member isolated from this family, phakellistatin19, an octacyclopeptide containing three Pro moieties and a high percentage of apolar residues. Exhaustive NMR studies on the synthetic and natural phakellistatin 19 have been performed in order to find a plausible explanation for this intriguing behavior. Moreover, taking advantage of phakellistatin's framework, analogues with different cis/trans geometry at the key prolyl peptide bonds were designed, covering a promising conformational space that could not be reached by the natural peptide. By introduction of proline surrogates (psi(Me,Me)pro residues) in phakellistatin 19, which effectively increases the percentage of cis conformation in the final peptides, this translates into enhanced biological activity, therefore "rescuing" an otherwise inactive cyclopeptide.

  DOI：

  10.1021/jm401520x
• 作为产物：
  描述：

  Fmoc-O-叔丁基-L-苏氨酸 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 FMOC-Thr(t-Bu)-F
  参考文献：
  名称：

  Rescuing Biological Activity from Synthetic Phakellistatin 19

  摘要：

  Phakellistatins is one of the families of Pro-rich cyclic peptides whose synthetic counterparts have revealed cytotoxicities that differ greatly from those displayed by their corresponding natural ones. This is also the case of the last member isolated from this family, phakellistatin19, an octacyclopeptide containing three Pro moieties and a high percentage of apolar residues. Exhaustive NMR studies on the synthetic and natural phakellistatin 19 have been performed in order to find a plausible explanation for this intriguing behavior. Moreover, taking advantage of phakellistatin's framework, analogues with different cis/trans geometry at the key prolyl peptide bonds were designed, covering a promising conformational space that could not be reached by the natural peptide. By introduction of proline surrogates (psi(Me,Me)pro residues) in phakellistatin 19, which effectively increases the percentage of cis conformation in the final peptides, this translates into enhanced biological activity, therefore "rescuing" an otherwise inactive cyclopeptide.

  DOI：

  10.1021/jm401520x

文献信息

• Carpino, Louis A.; Sadat-Aalaee, Dean; Chao, Hann Guang, Journal of the American Chemical Society, 1990, vol. 112, # 26, p. 9651 - 9652
  作者：Carpino, Louis A.、Sadat-Aalaee, Dean、Chao, Hann Guang、DeSelms, Robert H.

  DOI：——

  日期：——
• SYNTHESIS AND USE OF AMINO ACID FLUORIDES AS PEPTIDE COUPLING REAGENTS
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0496836B1

  公开（公告）日：1995-06-14
• US5360928A
  申请人：——

  公开号：US5360928A

  公开（公告）日：1994-11-01
• US5712418A
  申请人：——

  公开号：US5712418A

  公开（公告）日：1998-01-27
• US5750767A
  申请人：——

  公开号：US5750767A

  公开（公告）日：1998-05-12