(3S,7S,10S,13S)-7-benzyl-3-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-10-isopropyl-13-methyl-5,8,11-trioxo-1-phenyl-2,6,9,12-tetraazatetradecan-14-oic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (3S,7S,10S,13S)-7-benzyl-3-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-10-isopropyl-13-methyl-5,8,11-trioxo-1-phenyl-2,6,9,12-tetraazatetradecan-14-oic acid
• 英文别名: (2S)-2-[[(2S)-2-[[(2S)-2-[[(3S)-3-[(3aR,6S,6aR)-6-benzyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-(benzylamino)propanoyl]amino]-3-phenyl-propanoyl]amino]-3-methyl-butanoyl]amino]propanoic acid；(2S)-2-[[(2S)-2-[[(2S)-2-[[(3S)-3-[(3aR,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-(benzylamino)propanoyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]amino]propanoic acid
• 化学式: C₄₁H₅₂N₄O₉
• 分子量: 744.885
• InChiKey: FFYQWQOIWRIXMB-LWMPLDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  174
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3S,7S,10S,13S)-7-benzyl-3-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-10-isopropyl-13-methyl-5,8,11-trioxo-1-phenyl-2,6,9,12-tetraazatetradecan-14-oic acid 在 乙醇 、 palladium 10% on activated carbon 作用下， 以 环己烯 为溶剂， 反应 2.5h， 以44%的产率得到(2S)-2-((2S)-2-((2S)-2-((3S)-3-amino-3-((3aR,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)propanamido)-3-phenylpropanamido)-3-methylbutanamido)propanoic acid
  参考文献：
  名称：

  Linear and cyclic glycopeptide as HIV protease inhibitors

  摘要：

  Novel linear and cyclic glycotetrapeptides were designed, synthesized and tested for inhibition of the wild type C-SA HIV-1 protease enzyme. The incorporation of beta-amino acid sugar to the linear and cyclic peptides resulted in a series of fifteen novel compounds. Linear glycopeptide 4a and cyclic glycopeptide 6a displayed significant activities against the HIV protease enzyme. The experimental results were compared with a computational approach using molecular docking. The sugar hydroxyl group at the C-3 position in linear (4a) as well as cyclic glycopeptide (6a), shows hydrogen bonding interaction with the enzymatic Asp25/Asp25' residues in docking studies. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.018
• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-丙氨酸 、 、 Fmoc-L-苯丙氨酸 在 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以82%的产率得到(3S,7S,10S,13S)-7-benzyl-3-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-10-isopropyl-13-methyl-5,8,11-trioxo-1-phenyl-2,6,9,12-tetraazatetradecan-14-oic acid
  参考文献：
  名称：

  Linear and cyclic glycopeptide as HIV protease inhibitors

  摘要：

  Novel linear and cyclic glycotetrapeptides were designed, synthesized and tested for inhibition of the wild type C-SA HIV-1 protease enzyme. The incorporation of beta-amino acid sugar to the linear and cyclic peptides resulted in a series of fifteen novel compounds. Linear glycopeptide 4a and cyclic glycopeptide 6a displayed significant activities against the HIV protease enzyme. The experimental results were compared with a computational approach using molecular docking. The sugar hydroxyl group at the C-3 position in linear (4a) as well as cyclic glycopeptide (6a), shows hydrogen bonding interaction with the enzymatic Asp25/Asp25' residues in docking studies. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.018