(9H-fluoren-9-yl)methyl ((5S,8S,11S,14S,17S,20S,21R)-17-(tert-butoxymethyl)-5-(3-(dimethylamino)-3-oxopropyl)-8-isobutyl-11-isopropyl-3,14,21,23,23-pentamethyl-4,7,10,13,16,19-hexaoxo-2,22-dioxa-3,6,9,12,15,18-hexaazatetracosan-20-yl)carbamate | 1092982-18-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (9H-fluoren-9-yl)methyl ((5S,8S,11S,14S,17S,20S,21R)-17-(tert-butoxymethyl)-5-(3-(dimethylamino)-3-oxopropyl)-8-isobutyl-11-isopropyl-3,14,21,23,23-pentamethyl-4,7,10,13,16,19-hexaoxo-2,22-dioxa-3,6,9,12,15,18-hexaazatetracosan-20-yl)carbamate
• CAS: 1092982-18-7
• 化学式: C₅₃H₈₂N₈O₁₂
• 分子量: 1023.28
• InChiKey: OWHAEPCPPWYZBS-FPJIGDGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  73.0
• 可旋转键数：
  25.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  252.14
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl ((5S,8S,11S,14S,17S,20S,21R)-17-(tert-butoxymethyl)-5-(3-(dimethylamino)-3-oxopropyl)-8-isobutyl-11-isopropyl-3,14,21,23,23-pentamethyl-4,7,10,13,16,19-hexaoxo-2,22-dioxa-3,6,9,12,15,18-hexaazatetracosan-20-yl)carbamate 在 二乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Evaluation of peptide-aldehyde inhibitors using R188I mutant of SARS 3CL protease as a proteolysis-resistant mutant

  摘要：

  The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with Ile at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a K(m) of 33.8 mu M and k(cat) of 4753 s (1). Compared with the value reported for the mature protease containing a C-terminal His-tag, the relative activity of the mutant was nearly 10(6). Novel peptide-aldehyde derivatives containing a side-chain-protected C-terminal Gln efficiently inhibited the catalytic activity of the R188I mutant. The results indicated for the first time that the tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.057
• 作为产物：
  描述：

  、 Fmoc-O-叔丁基-L-苏氨酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以0.40 g的产率得到(9H-fluoren-9-yl)methyl ((5S,8S,11S,14S,17S,20S,21R)-17-(tert-butoxymethyl)-5-(3-(dimethylamino)-3-oxopropyl)-8-isobutyl-11-isopropyl-3,14,21,23,23-pentamethyl-4,7,10,13,16,19-hexaoxo-2,22-dioxa-3,6,9,12,15,18-hexaazatetracosan-20-yl)carbamate
  参考文献：
  名称：

  Evaluation of peptide-aldehyde inhibitors using R188I mutant of SARS 3CL protease as a proteolysis-resistant mutant

  摘要：

  The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with Ile at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a K(m) of 33.8 mu M and k(cat) of 4753 s (1). Compared with the value reported for the mature protease containing a C-terminal His-tag, the relative activity of the mutant was nearly 10(6). Novel peptide-aldehyde derivatives containing a side-chain-protected C-terminal Gln efficiently inhibited the catalytic activity of the R188I mutant. The results indicated for the first time that the tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.057