versicoloritide B | 1334715-68-2

• 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: versicoloritide B
• 英文别名: cyclo-(Gly-cis-L-Pro-L-Phe-cis-L-Pro-L-Phe)；(3S,6S,12S,18S)-3,12-dibenzyl-1,4,10,13,16-pentazatricyclo[16.3.0.06,10]henicosane-2,5,11,14,17-pentone
• CAS: 1334715-68-2
• 化学式: C₃₀H₃₅N₅O₅
• 分子量: 545.638
• InChiKey: HOYUVNRHMGMLTE-QORCZRPOSA-N

物化性质

• 沸点：
  938.7±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  versicoloritide B 在 盐酸 、 水 作用下， 反应 20.0h， 生成 甘氨酸盐酸盐 、 L-苯丙氨酸盐酸盐 、 L-脯氨酸盐酸盐
  参考文献：
  名称：

  Cyclopeptides and polyketides from coral-associated fungus, Aspergillus versicolor LCJ-5-4

  摘要：

  Three new cyclopentapeptides, versicoloritides A-C (1-3), a new orcinol tetramer, tetraorcinol A (4), and two new lactones, versicolactones A and B (5 and 6) together with three known metabolites, diorcinol, glyantrypine, and cordyol C were isolated from the fermentation broth of the coral-associated fungus Aspergillus versicolor LCJ-5-4. Their structures were elucidated by spectroscopic and chemical methods. The new compounds 1-4 were evaluated for their radical-scavenging activity and antimicrobial activity against Staphylococcus aureus, Escherichia coli, Enterobacter aerogenes, Bacillus subtilis, Pseudomonas aeruginosa, and Candida albicans and cytotoxicity against P388 and Hela cell lines. Compound 4 showed weak radical-scavenging activity against the DPPH radical with an IC50 value of 67 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.003
• 作为产物：
  描述：

  Fmoc-L-苯丙氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 versicoloritide B
  参考文献：
  名称：

  Synthesis of the All-l Cyclopentapeptides Versicoloritides A, B, and C

  摘要：

  Herein we describe the first synthesis of the all-L naturally occurring cyclopentapeptides versicoloritides A, B, and C. We found that the extent of oligomerization and epimerization upon head-to-tail cyclization of the linear pentapeptide precursors could be reduced to acceptable levels by modifying the reaction conditions.

  DOI：

  10.1055/s-0032-1316994

文献信息

• Cyclopeptides and polyketides from coral-associated fungus, Aspergillus versicolor LCJ-5-4
  作者：Yibin Zhuang、Xiancun Teng、Yi Wang、Peipei Liu、Hui Wang、Jing Li、Guoqiang Li、Weiming Zhu

  DOI：10.1016/j.tet.2011.07.003

  日期：2011.9

  Three new cyclopentapeptides, versicoloritides A-C (1-3), a new orcinol tetramer, tetraorcinol A (4), and two new lactones, versicolactones A and B (5 and 6) together with three known metabolites, diorcinol, glyantrypine, and cordyol C were isolated from the fermentation broth of the coral-associated fungus Aspergillus versicolor LCJ-5-4. Their structures were elucidated by spectroscopic and chemical methods. The new compounds 1-4 were evaluated for their radical-scavenging activity and antimicrobial activity against Staphylococcus aureus, Escherichia coli, Enterobacter aerogenes, Bacillus subtilis, Pseudomonas aeruginosa, and Candida albicans and cytotoxicity against P388 and Hela cell lines. Compound 4 showed weak radical-scavenging activity against the DPPH radical with an IC50 value of 67 mu M. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of the All-l Cyclopentapeptides Versicoloritides A, B, and C
  作者：Margaret Brimble、Harveen Kaur、Amanda Heapy

  DOI：10.1055/s-0032-1316994

  日期：——

  Herein we describe the first synthesis of the all-L naturally occurring cyclopentapeptides versicoloritides A, B, and C. We found that the extent of oligomerization and epimerization upon head-to-tail cyclization of the linear pentapeptide precursors could be reduced to acceptable levels by modifying the reaction conditions.