tawicyclamide A | 143007-28-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: tawicyclamide A
• 英文别名: (2R,5R,9S,16S,19S,25S)-9-benzyl-2-butan-2-yl-16,25-di(propan-2-yl)-7,14,30-trithia-3,10,17,23,26,31,32,33-octazapentacyclo[26.2.1.15,8.112,15.019,23]tritriaconta-1(31),8(33),12,15(32),28-pentaene-4,11,18,24,27-pentone
• CAS: 143007-28-7
• 化学式: C₃₉H₅₀N₈O₅S₃
• 分子量: 807.075
• InChiKey: RGYATJKXBBMJQJ-UVEJMCTASA-N

物化性质

• 沸点：
  1092.8±65.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  55
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  257
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tawicyclamide A 在 nickel(IV) oxide 作用下， 以 苯 为溶剂， 反应 23.0h， 以26%的产率得到dehydrotawicyclamide A
  参考文献：
  名称：

  Tawicyclamides A and B, new cyclic peptides from the Ascidian Lissoclinum patella: studies on the solution- and solid-state conformations

  摘要：

  Two new cytotoxic cyclic peptides, tawicyclamides A and B (1-2), were isolated from the ascidian Lissoclinum patella collected in the Philippine Islands and their structures determined by NMR spectroscopy, oxidation studies, and tandem mass spectrometry. Absolute configurations were determined by HPLC analysis of derivatized constituent amino acids obtained from acid hydrolysis. X-ray crystallography confirmed the structure of tawicylamide B and showed that the compound assumes an unusual conformation facilitated by a cis-valine-praline amide bond and stabilized by an intramolecular hydrogen bond. Tawicyclamides A and B represent a new family of cyclic octapeptides, possessing thiazole and thiazoline amino acids but lacking the oxazoline ring characteristic of previously reported cyclic peptides from L. patella. Isomerization of the valine-proline amide bond from cis to trans is among the conformational changes occurring upon oxidation of the thiazoline ring to a thiazole. A variety of NMR data supports these changes. Molecular modeling studies allowed us to establish the solution conformations of these compounds and to evaluate these conformational interpretations. Tawicyclamides A and B were weakly but equally cytotoxic against human colon tumor cells in vitro.

  DOI：

  10.1021/jo00043a017