kahalalide B | 180714-95-8

• 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: kahalalide B
• 英文别名: N-[(2S)-1-[[(3R,6S,9R,16S,19S)-6-benzyl-16-[(1R)-1-hydroxyethyl]-3-(2-methylpropyl)-2,5,8,12,15,18-hexaoxo-11-oxa-1,4,7,14,17-pentazabicyclo[17.3.0]docosan-9-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-5-methylhexanamide
• CAS: 180714-95-8
• 化学式: C₄₅H₆₃N₇O₁₁
• 分子量: 878.036
• InChiKey: VZOXBTHPDCYYBY-MSGUKBQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  63
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  262
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  deamino-hLeu-Tyr-D-Ser-Phe-D-Leu-Pro-Thr-Gly-SBn 在 咪唑 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以98%的产率得到kahalalide B
  参考文献：
  名称：

  Macrolactonization of Peptide Thioesters Catalyzed by Imidazole and Its Application in the Synthesis of Kahalalide B and Analogues

  摘要：

  The macrolactonization of peptide thioester to yield cyclic depsipeptides was developed using imidazole as a catalyst. This strategy was applied to the synthesis of kahalalide B and its analogues.

  DOI：

  10.1021/ol100596p

文献信息

• Depsipeptide synthesis using a late-stage Ag(<scp>i</scp>)-promoted macrolactonisation of peptide thioamides
  作者：Sadegh Shabani、Craig A. Hutton

  DOI：10.1039/d0cc07747j

  日期：——

  often challenging due to the low nucleophilicity of hydroxyl groups, epimerisation, cyclodimerisation, and potential acyl transfer reactions of the ester. Herein, we report a novel macrolactonisation strategy employing a Ag(I)-promoted conversion of peptide thioamides to isoimide intermediates, which undergo site-selective intramolecular acyl transfer to serine/threonine side chains to generate the macrolactone

  由于羟基的低亲核性，差向异构化，环二聚化和酯的潜在酰基转移反应，使肽大环内酯化以生成环状二肽通常是具有挑战性的。在本文中，我们报道了一种新型的大内酯化策略，该策略采用了由Ag（I）促进的肽硫代酰胺向异酰亚胺中间体的转化，该中间体经过位点选择性分子内酰基转移到丝氨酸/苏氨酸侧链以生成大内酯。
• Macrolactonization of Peptide Thioesters Catalyzed by Imidazole and Its Application in the Synthesis of Kahalalide B and Analogues
  作者：Yangmei Li、Marc Giulionatti、Richard A. Houghten

  DOI：10.1021/ol100596p

  日期：2010.5.21

  The macrolactonization of peptide thioester to yield cyclic depsipeptides was developed using imidazole as a catalyst. This strategy was applied to the synthesis of kahalalide B and its analogues.