(2S,7S,E)-tert-butyl 7-(tert-butoxycarbonylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-7-(methoxycarbonyl)hept-4-enoate | 1261295-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,7S,E)-tert-butyl 7-(tert-butoxycarbonylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-7-(methoxycarbonyl)hept-4-enoate
• 英文别名: 8-O-tert-butyl 1-O-methyl (E,2S,7S)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]oct-4-enedioate
• CAS: 1261295-47-9
• 化学式: C₃₃H₄₂N₂O₈
• 分子量: 594.705
• InChiKey: QWKOQAAOOITGSE-UHFAIGRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,7S,E)-tert-butyl 7-(tert-butoxycarbonylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-7-(methoxycarbonyl)hept-4-enoate 在 palladium 10% on activated carbon 、 氢气 、 三甲基氢氧化锡 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 32.0h， 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
• 作为产物：
  描述：

  Fmoc-L-烯丙基甘氨酸 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 叔丁基三氯乙酰亚胺酯 作用下， 以 二氯甲烷 、 环己烷 、 乙酸乙酯 为溶剂， 反应 89.5h， 生成 (2S,7S,E)-tert-butyl 7-(tert-butoxycarbonylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-7-(methoxycarbonyl)hept-4-enoate
  参考文献：
  名称：

  Synthesis of Orthogonally Protected Disulfide Bridge Mimetics

  摘要：

  Concise routes to four orthogonally protected, enantiopure disulfide bridge mimetics are reported. These four dicarba analogues possess an alkyne, an (E)-alkene, a (Z)-alkene, and an alkane as substitutes for the disulfide bridge. Selective deprotection of one of these mimetics is also illustrated.

  DOI：

  10.1021/jo1018427

文献信息

• Synthesis of Orthogonally Protected Disulfide Bridge Mimetics
  作者：Andrew C. Tadd、Kristian Meinander、Kristina Luthman、Erik A. A. Wallén

  DOI：10.1021/jo1018427

  日期：2011.1.21

  Concise routes to four orthogonally protected, enantiopure disulfide bridge mimetics are reported. These four dicarba analogues possess an alkyne, an (E)-alkene, a (Z)-alkene, and an alkane as substitutes for the disulfide bridge. Selective deprotection of one of these mimetics is also illustrated.
• Replacement of the Disulfide Bridge in a KLK3-Stimulating Peptide Using Orthogonally Protected Building Blocks
  作者：Kristian Meinander、Miikka Pakkala、Janne Weisell、Ulf-Håkan Stenman、Hannu Koistinen、Ale Närvänen、Erik A. A. Wallén

  DOI：10.1021/ml400419g

  日期：2014.2.13

  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.