Cbz-MeIle-MeAla-NHNH-Boc | 383396-83-6

• 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: Cbz-MeIle-MeAla-NHNH-Boc
• CAS: 383396-83-6
• 化学式: C₂₄H₃₈N₄O₆
• 分子量: 478.589
• InChiKey: LERXMYSZYPYQQK-LNLFQRSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  117.28
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Cbz-MeIle-MeAla-NHNH-Boc 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 74.0h， 生成 (1'S,3S,6S)-1,4,6-trimethyl-3-(1-methylpropyl)-2,5-piperazinedione
  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+
• 作为产物：
  描述：

  Cbz-MeAla-NHNH-Boc 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 Cbz-MeIle-MeAla-NHNH-Boc
  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+