methyl (2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,4S)-4-hydroxy-1-[2-methyl-2-(tetradecanoylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-4-methyl-pentanoyl]amino]-3-methyl-butanoyl]amino]-5-oxo-pentanoyl]amino]-4-methyl-pentanoate

• 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: methyl (2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,4S)-4-hydroxy-1-[2-methyl-2-(tetradecanoylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-4-methyl-pentanoyl]amino]-3-methyl-butanoyl]amino]-5-oxo-pentanoyl]amino]-4-methyl-pentanoate
• 英文别名: methyl (2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,4S)-4-hydroxy-1-[2-methyl-2-(tetradecanoylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]amino]-4-methylpentanoate
• 化学式: C₄₆H₈₃N₇O₁₀
• 分子量: 894.206
• InChiKey: NUIAISTUQFRGSJ-YIEWUAFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  63
• 可旋转键数：
  32
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  255
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,4S)-4-hydroxy-1-[2-methyl-2-(tetradecanoylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-4-methyl-pentanoyl]amino]-3-methyl-butanoyl]amino]-5-oxo-pentanoyl]amino]-4-methyl-pentanoate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以82%的产率得到(S)-2-[(S)-2-((S)-2-{[(2S,4S)-4-Hydroxy-1-(2-methyl-2-tetradecanoylamino-propionyl)-pyrrolidine-2-carbonyl]-amino}-4-methyl-pentanoylamino)-3-methyl-butyrylamino]-pentanedioic acid 5-amide 1-[((S)-1-hydroxymethyl-3-methyl-butyl)-amide]
  参考文献：
  名称：

  Synthesis and structure–activity relationships of the halovirs, antiviral natural products from a marine-derived fungus

  摘要：

  The halovirs are linear, lipophilic peptides produced by a marine-derived fungus of the genus Seytalidium. We recently reported that these molecules possess potent in vitro activity against the herpes simplex viruses I and 2. Here we present structure-activity relationships defining key structural elements for optimal viral inhibition. Results demonstrate that an N-alpha-acyl chain of at least 14 carbons and an Aib-Pro dipeptide are critical for maintaining the antiviral activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.044
• 作为产物：
  描述：

  Boc-L-谷氨酰胺 在 三氟乙酸 作用下， 反应 0.33h， 生成 methyl (2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,4S)-4-hydroxy-1-[2-methyl-2-(tetradecanoylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-4-methyl-pentanoyl]amino]-3-methyl-butanoyl]amino]-5-oxo-pentanoyl]amino]-4-methyl-pentanoate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of the halovirs, antiviral natural products from a marine-derived fungus

  摘要：

  The halovirs are linear, lipophilic peptides produced by a marine-derived fungus of the genus Seytalidium. We recently reported that these molecules possess potent in vitro activity against the herpes simplex viruses I and 2. Here we present structure-activity relationships defining key structural elements for optimal viral inhibition. Results demonstrate that an N-alpha-acyl chain of at least 14 carbons and an Aib-Pro dipeptide are critical for maintaining the antiviral activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.044