(S)-2-((S)-2-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-hydroxy-propionylamino)-3-hydroxy-butyrylamino]-4-methyl-pentanoylamino}-3-carbamoyl-propionylamino)-3-phenyl-propionic acid | 183872-44-8

• 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: (S)-2-((S)-2-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-hydroxy-propionylamino)-3-hydroxy-butyrylamino]-4-methyl-pentanoylamino}-3-carbamoyl-propionylamino)-3-phenyl-propionic acid
• 英文别名: (2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-amino-3-hydroxy-propanoyl]amino]-3-hydroxy-butanoyl]amino]-4-methyl-pentanoyl]amino]-4-oxo-butanoyl]amino]-3-phenyl-propanoic acid；(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoic acid
• CAS: 183872-44-8
• 化学式: C₂₆H₄₀N₆O₉
• 分子量: 580.638
• InChiKey: CEGOOPMAJUYOFS-BBIZDQJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  263
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-{(S)-2-[(2S,3R)-2-((S)-2-Amino-3-hydroxy-propionylamino)-3-hydroxy-butyrylamino]-4-methyl-pentanoylamino}-3-carbamoyl-propionylamino)-3-phenyl-propionic acid 、 C₅₅H₇₉N₉O₁₄ 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 HO-Phe-Asn-Leu-Thr-Ser-NH-C(=O)-(CH2)5-Ethyne-(CH2)5-C(=O)-N-Pro-Gln-Ile-Thr-Leu-Trp-OH
  参考文献：
  名称：

  Restricting the flexibility of crosslinked, interfacial peptide inhibitors of HIV-1 protease

  摘要：

  Interfacial peptides of HIV-1 protease were crosslinked with varying length alkyl-chains containing either a single cia or trans double bond, or a triple bond to remove degrees of freedom within the tethers. The synthesis of these compounds and their effects on the activity of HIV-1 protease are described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00595-2

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.
• Targeting the Dimerization Interface of HIV-1 Protease:  Inhibition with Cross-Linked Interfacial Peptides
  作者：Reena Zutshi、Jeff Franciskovich、Michael Shultz、Barbara Schweitzer、Patricia Bishop、Matt Wilson、Jean Chmielewski

  DOI：10.1021/ja962496j

  日期：1997.5.1

  Agents have been designed and synthesized which target the dimerization interface of HIV-1 protease. These agents, which contain cross-linked peptides from the N- and C-termini of the protease, both inhibit HIV-1 protease activity and decrease the amount of protease dimer in solution as measured by size exclusion chromatography, protein crosslinking, and protease fluorescence studies. Additionally we have shown that active site-targeted agents inhibit HIV-1 protease activity but have little effect on protease dimerization. These data support the claim that inhibition with the crosslinked agents is based on a decrease in the amount of protease homodimer in solution which in turn is responsible for a decrease in the activity of the protease.
• Restricting the flexibility of crosslinked, interfacial peptide inhibitors of HIV-1 protease
  作者：Luckner G. Ulysse、Jean Chmielewski

  DOI：10.1016/s0960-894x(98)00595-2

  日期：1998.11

  Interfacial peptides of HIV-1 protease were crosslinked with varying length alkyl-chains containing either a single cia or trans double bond, or a triple bond to remove degrees of freedom within the tethers. The synthesis of these compounds and their effects on the activity of HIV-1 protease are described. (C) 1998 Elsevier Science Ltd. All rights reserved.