(2S,7S)-8-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-7-((9H-fluoren-9-yl)methoxycarbonylamino)heptanoic acid | 1516886-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,7S)-8-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-7-((9H-fluoren-9-yl)methoxycarbonylamino)heptanoic acid
• CAS: 1516886-37-5
• 化学式: C₃₂H₄₂N₂O₈
• 分子量: 582.694
• InChiKey: VGPDIDQMIBHOFI-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140.26
• 氢给体数：
  3.0
• 氢受体数：
  7.0

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 、 (2S,7S)-8-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-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1%的产率得到(2S,5S,8S,11S,14S,17S,20S,23S,26S,29S,32S,37S)-37-amino-14-(2-amino-2-oxoethyl)-5-benzyl-20-(carboxymethyl)-17,23-bis[(4-hydroxyphenyl)methyl]-11-(1H-imidazol-5-ylmethyl)-8-methyl-26-(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,38-undecaoxo-2,29-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclooctatriacontane-32-carboxylic 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
• 作为产物：
  描述：

  N-Boc-L-烯丙基甘氨酸甲酯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 、 三甲基氢氧化锡 作用下， 以 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 38.0h， 生成 (2S,7S)-8-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-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