homodestruxin B | 110538-19-7

• 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: homodestruxin B
• 英文别名: cyclo[N(Me)Ala-bAla-D-OLeu-Pro-Ile-N(Me)Ile]；(3R,10S,13S,16S,19S)-13,16-bis[(2S)-butan-2-yl]-10,11,14-trimethyl-3-(2-methylpropyl)-4-oxa-1,8,11,14,17-pentazabicyclo[17.3.0]docosane-2,5,9,12,15,18-hexone
• CAS: 110538-19-7
• 化学式: C₃₁H₅₃N₅O₇
• 分子量: 607.791
• InChiKey: WWALEZSSEHJILM-AMKJHPCNSA-N

物化性质

• 沸点：
  879.6±65.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  homodestruxin B 在 leaves of Sinapis alba cultivar Ochre 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 生成 hydroxyhomodestruxin B
  参考文献：
  名称：

  Metabolism of the Host-Selective Toxins Destruxin B and Homodestruxin B:  Probing a Plant Disease Resistance Trait

  摘要：

  [GRAPHICS]Metabolism of the host-selective toxins destruxin B (1) and homodestruxin B (2) by plants resistant and susceptible to Alternaria blackspot (caused by the fungal pathogen Alternaria brassicae (Berk,) Sacc,) was established using synthetic radiolabeied compounds. The toxins are transformed into the less phytotoxic hydroxydestruxins 3 and 4. The rate of metabolic transformation was correlated with the plant's disease resistance, i.e., significantly faster rates were observed for plants resistant to the pathogen, Efficient syntheses of 1, 2, 3, and 4 are described.

  DOI：

  10.1021/ol991042z
• 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 homodestruxin 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

• Metabolism of the Host-Selective Toxins Destruxin B and Homodestruxin B:  Probing a Plant Disease Resistance Trait
  作者：M. Soledade C. Pedras、Irina. L. Zaharia、Yuanzhu Gai、Kevin C. Smith、Dale E. Ward

  DOI：10.1021/ol991042z

  日期：1999.11.1

  [GRAPHICS]Metabolism of the host-selective toxins destruxin B (1) and homodestruxin B (2) by plants resistant and susceptible to Alternaria blackspot (caused by the fungal pathogen Alternaria brassicae (Berk,) Sacc,) was established using synthetic radiolabeied compounds. The toxins are transformed into the less phytotoxic hydroxydestruxins 3 and 4. The rate of metabolic transformation was correlated with the plant's disease resistance, i.e., significantly faster rates were observed for plants resistant to the pathogen, Efficient syntheses of 1, 2, 3, and 4 are described.
• 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.