(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[7-[[7-[(2S)-2-[[(2S)-5-amino-1-[[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-7-oxoheptyl]amino]heptanoylamino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoic acid

• 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: (2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[7-[[7-[(2S)-2-[[(2S)-5-amino-1-[[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-7-oxoheptyl]amino]heptanoylamino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoic acid
• 化学式: C₇₇H₁₁₉N₁₅O₂₀
• 分子量: 1574.88
• InChiKey: CCMZOAFFKUJJHN-XTDBVNKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  112
• 可旋转键数：
  53
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  561
• 氢给体数：
  19
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  (2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[7-[[7-[(2S)-2-[[(2S)-5-amino-1-[[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-7-oxoheptyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]heptanoylamino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以68%的产率得到(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[7-[[7-[(2S)-2-[[(2S)-5-amino-1-[[(2S,3S)-1-[[(2S,3R)-1-[[(2S)-1-[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-7-oxoheptyl]amino]heptanoylamino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  Hydrophobicity versus activity in crosslinked interfacial peptide inhibitors of HIV-1 protease

  摘要：

  Crosslinked peptides with amino functionality incorporated within the tethering moiety 2a-c, 3a-c were synthesized and tested as interfacial inhibitors of HIV-1 protease. As part of a strategy to develop the novel method of dissociative inhibition as a viable pharmacological approach, compounds were made to test hydrophobicity and size requirements of the tethering moiety. In the case of crosslinked interfacial peptide inhibitors of HIV-1 protease, hydrophilic 2a-c and bulky hydrophobic 3a-c tethers decreased effectiveness by approximately 10- and 2-fold, respectively. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00572-7

文献信息

• Hydrophobicity versus activity in crosslinked interfacial peptide inhibitors of HIV-1 protease
  作者：Michael D. Shultz、Jean Chmielewski

  DOI：10.1016/s0957-4166(97)00572-7

  日期：1997.12

  Crosslinked peptides with amino functionality incorporated within the tethering moiety 2a-c, 3a-c were synthesized and tested as interfacial inhibitors of HIV-1 protease. As part of a strategy to develop the novel method of dissociative inhibition as a viable pharmacological approach, compounds were made to test hydrophobicity and size requirements of the tethering moiety. In the case of crosslinked interfacial peptide inhibitors of HIV-1 protease, hydrophilic 2a-c and bulky hydrophobic 3a-c tethers decreased effectiveness by approximately 10- and 2-fold, respectively. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.