去甲基绿僵菌素 B | 27482-48-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 中文名称: 去甲基绿僵菌素 B
• 中文别名: 去甲基绿僵菌素B
• 英文名称: desmethyldestruxin B
• 英文别名: 3-L-Valinedestruxin B；(3R,10S,13S,16S,19S)-16-[(2S)-butan-2-yl]-10,11-dimethyl-3-(2-methylpropyl)-13-propan-2-yl-4-oxa-1,8,11,14,17-pentazabicyclo[17.3.0]docosane-2,5,9,12,15,18-hexone
• CAS: 27482-48-0
• 化学式: C₂₉H₄₉N₅O₇
• 分子量: 579.737
• InChiKey: LKJMCPAAJZITNV-OCCJOITDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  154
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-2-羟基-4-甲基戊酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 59.75h， 生成 去甲基绿僵菌素 B
  参考文献：
  名称：

  Probing Host-Selective Phytotoxicity:  Synthesis of Destruxin B and Several Natural Analogues

  摘要：

  The syntheses of the host-selective phytotoxin destruxin B [cyclo(beta Ala-Hmp-Pro-Ile-MeVal-MeAla), Hmp = (2R)-2-hydroxy-4-methylpentanoic acid], and the closely related natural analogues homodestruxin B (MeVal --> MeIle), desmethyldestruxin B (MeVal --> Val), hydroxydestruxin B (Hmp --> Dhmp, Dhmp = (2R)-2,4-dihydroxy-4-methylpentanoic acid), and hydroxyhomodestruxin B (MeVal --> MeIle, Hmp-Dhmp) are described. In each case, the MeAla-beta Ala linkage was formed by cyclization and the precursor linear hexadepsipeptides were formed by condensing two three-residue fragments. Radiolabeled samples of destruxin B, homodestruxin B, and hydroxydestruxin B were prepared by coupling [3-C-14]-beta -alanine to the appropriate pentadepsipeptide followed by cyclization. A noteworthy feature of the synthesis involves the novel use of a Boc-hydrazide protecting group on dipeptides with a C-terminal N-methylalanine residue to inhibit the otherwise facile dioxopiperazine formation during peptide coupling.

  DOI：

  10.1021/jo015953+

文献信息

• Probing Host-Selective Phytotoxicity:  Synthesis of Destruxin B and Several Natural Analogues
  作者：Dale E. Ward、Yuanzhu Gai、Ryszard Lazny、M. Soledade C. Pedras

  DOI：10.1021/jo015953+

  日期：2001.11.1

  The syntheses of the host-selective phytotoxin destruxin B [cyclo(beta Ala-Hmp-Pro-Ile-MeVal-MeAla), Hmp = (2R)-2-hydroxy-4-methylpentanoic acid], and the closely related natural analogues homodestruxin B (MeVal --> MeIle), desmethyldestruxin B (MeVal --> Val), hydroxydestruxin B (Hmp --> Dhmp, Dhmp = (2R)-2,4-dihydroxy-4-methylpentanoic acid), and hydroxyhomodestruxin B (MeVal --> MeIle, Hmp-Dhmp) are described. In each case, the MeAla-beta Ala linkage was formed by cyclization and the precursor linear hexadepsipeptides were formed by condensing two three-residue fragments. Radiolabeled samples of destruxin B, homodestruxin B, and hydroxydestruxin B were prepared by coupling [3-C-14]-beta -alanine to the appropriate pentadepsipeptide followed by cyclization. A noteworthy feature of the synthesis involves the novel use of a Boc-hydrazide protecting group on dipeptides with a C-terminal N-methylalanine residue to inhibit the otherwise facile dioxopiperazine formation during peptide coupling.