(2S,5S,8S,11S,14S,17S,20S,23S,26S,29S,32S,34E,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-undecazacyclooctatriacont-34-ene-32-carboxylic acid | 1516886-27-3

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: (2S,5S,8S,11S,14S,17S,20S,23S,26S,29S,32S,34E,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-undecazacyclooctatriacont-34-ene-32-carboxylic acid
• CAS: 1516886-27-3
• 化学式: C₆₈H₉₁N₁₅O₁₈
• 分子量: 1406.56
• InChiKey: GFKCCVDDTYADLF-OHUIZNPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  101
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  533
• 氢给体数：
  18
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 (2S,7S,E)-8-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-7-((9H-fluoren-9-yl)methoxycarbonylamino)hept-4-enoic 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5%的产率得到(2S,5S,8S,11S,14S,17S,20S,23S,26S,29S,32S,34E,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-undecazacyclooctatriacont-34-ene-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

文献信息

• 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.