aerucyclamide B | 1037291-11-4

• 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: aerucyclamide B
• 英文别名: (4S,7R,8S,18R)-4,18-bis[(2S)-butan-2-yl]-7-methyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexazatetracyclo[17.2.1.15,8.112,15]tetracosa-1(21),5(24),12(23),14,19(22)-pentaene-2,9,16-trione
• CAS: 1037291-11-4
• 化学式: C₂₄H₃₂N₆O₄S₂
• 分子量: 532.688
• InChiKey: JFWABYMXSVHLEW-ZUDVWZRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  191
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  aerucyclamide A 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 1.5h， 以16%的产率得到aerucyclamide B
  参考文献：
  名称：

  Aerucyclamides A and B: Isolation and Synthesis of Toxic Ribosomal Heterocyclic Peptides from the Cyanobacterium Microcystis aeruginosa PCC 7806

  摘要：

  Two new modified hexacyclopeptides, aerucyclamides A and B, were isolated from the toxic freshwater cyanobacterium Microcystis aeruginosa PCC 7806. The constitution was assigned by spectroscopic methods, and the configuration determined by chemical degradation and analysis by Marfey's method combined with chemical synthesis. Synthetic aerucyclamide B was obtained through oxidation of aerucyclamide A (MnO(2), benzene). The aerucyclamides were found to be toxic to the freshwater crustacean Thamnocephalus platyurus, exhibiting LC(50) values for congeners A and B of 30.5 and 33.8 mu M, respectively.

  DOI：

  10.1021/np800118g

文献信息

• First total synthesis of aerucyclamide B
  作者：Stella Peña、Laura Scarone、Eduardo Manta、Gloria Serra

  DOI：10.1016/j.tetlet.2013.03.060

  日期：2013.5

  The first total synthesis of the antimalarial aerucyclamide B has been achieved in 9% overall yield. Two thiazoles and a dipeptide were used to prepare two open precursors of cyclo-Gly-L-allo-Thr-L-Ile-Thz-D-allo-Ile-Thz. Cyclodehydration with Deoxo-Fluor of the beta-hydroxyamide present in the macrocycle, rendered aerucyclamide B (67%) and an unexpected fluorous derivative (28%). (C)13 Elsevier Ltd. All rights reserved.
• Aerucyclamides A and B: Isolation and Synthesis of Toxic Ribosomal Heterocyclic Peptides from the Cyanobacterium <i>Microcystis aeruginosa</i> PCC 7806
  作者：Cyril Portmann、Judith F. Blom、Karl Gademann、Friedrich Jüttner

  DOI：10.1021/np800118g

  日期：2008.7.1

  Two new modified hexacyclopeptides, aerucyclamides A and B, were isolated from the toxic freshwater cyanobacterium Microcystis aeruginosa PCC 7806. The constitution was assigned by spectroscopic methods, and the configuration determined by chemical degradation and analysis by Marfey's method combined with chemical synthesis. Synthetic aerucyclamide B was obtained through oxidation of aerucyclamide A (MnO(2), benzene). The aerucyclamides were found to be toxic to the freshwater crustacean Thamnocephalus platyurus, exhibiting LC(50) values for congeners A and B of 30.5 and 33.8 mu M, respectively.