(S)-7-(tert-butoxycarbonyl)-7-((9H-fluoren-9-yl)methoxycarbonylamino)heptanoic acid | 1516886-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-7-(tert-butoxycarbonyl)-7-((9H-fluoren-9-yl)methoxycarbonylamino)heptanoic acid
• CAS: 1516886-38-6
• 化学式: C₂₇H₃₃NO₆
• 分子量: 467.562
• InChiKey: JYHZBSJNJZHYSL-QHCPKHFHSA-N

物化性质

• 沸点：
  645.1±55.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 (S)-7-(tert-butoxycarbonyl)-7-((9H-fluoren-9-yl)methoxycarbonylamino)heptanoic acid 、 Fmoc-L-酪氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-L-天冬氨酸 、 N-芴甲氧羰基-L-组氨酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以0.6%的产率得到N(1)Val-Phe-Ala-His-Asn-Tyr-Asp-Tyr-Leu-Val-Asu(1)-OH
  参考文献：
  名称：

  Replacement of the Disulfide Bridge in a KLK3-Stimulating Peptide Using Orthogonally Protected Building Blocks

  摘要：

  Peptide "B-2", which is one of the most potent kallikrein-related peptidase 3 (KLK3)-stimulating compounds, consists of 12 amino acids and is cyclized by a disulfide bridge between the N- and C-terminal cysteines. Orthogonally protected building blocks were used in the peptide synthesis to introduce a disulfide bridge mimetic consisting of four carbon atoms. The resulting pseudopeptides with alkane and E-alkene linkers doubled the proteolytic activity of KLK3 at a concentration of 14 mu M. They were almost as potent as the parent "B-2" peptide, which gives a 3.6-fold increase in the proteolytic activity of KLK3 at the same concentration.

  DOI：

  10.1021/ml400419g
• 作为产物：
  描述：

  (S)-1-tert-butyl 2-((9H-fluoren-9-yl)methoxycarbonylamino)-7-methoxycarbonylheptanoate 在 三甲基氢氧化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以41%的产率得到(S)-7-(tert-butoxycarbonyl)-7-((9H-fluoren-9-yl)methoxycarbonylamino)heptanoic acid
  参考文献：
  名称：

  Replacement of the Disulfide Bridge in a KLK3-Stimulating Peptide Using Orthogonally Protected Building Blocks

  摘要：

  Peptide "B-2", which is one of the most potent kallikrein-related peptidase 3 (KLK3)-stimulating compounds, consists of 12 amino acids and is cyclized by a disulfide bridge between the N- and C-terminal cysteines. Orthogonally protected building blocks were used in the peptide synthesis to introduce a disulfide bridge mimetic consisting of four carbon atoms. The resulting pseudopeptides with alkane and E-alkene linkers doubled the proteolytic activity of KLK3 at a concentration of 14 mu M. They were almost as potent as the parent "B-2" peptide, which gives a 3.6-fold increase in the proteolytic activity of KLK3 at the same concentration.

  DOI：

  10.1021/ml400419g