cycloreticulin C | 1105703-78-3

• 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: cycloreticulin C
• 英文别名: cyclo(Pro-Gly-Gln-Pro-Pro-Tyr-Val)；cyclo[Gln-Pro-Pro-Tyr-Val-Pro-Gly]；3-[(3S,9S,15S,21S,24S,27S)-24-[(4-hydroxyphenyl)methyl]-2,8,11,14,20,23,26-heptaoxo-21-propan-2-yl-1,7,10,13,19,22,25-heptazatetracyclo[25.3.0.03,7.015,19]triacontan-9-yl]propanamide
• CAS: 1105703-78-3
• 化学式: C₃₆H₅₀N₈O₉
• 分子量: 738.841
• InChiKey: JPOCRGHRLGVHLD-CJQGIMJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  241
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  cycloreticulin C 、 异丙醇 、 三氟乙酸酐 在 盐酸 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 27.33h， 生成 propan-2-yl (2S)-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate 、 Isopropyl [(trifluoroacetyl)amino]acetate 、 (S)-3-Methyl-2-(2,2,2-trifluoro-acetylamino)-butyric acid isopropyl ester
  参考文献：
  名称：

  3D-structure of cycloreticulin C and glabrin A, cyclopeptides from the seeds of Annona reticulata

  摘要：

  Two cyclopeptides, the cycloheptapeptide cycloreticulin C, cyclo(Pro(1)-Gly(2)-Gln(3)-Pro(4)-Pro(5)-Tyr(6)-Val(7)) (1), and the cyclohexapeptide glabrin A, cyclo(Pro(1)-Gly(2)-Leu(3)-Val(4)-Ile(5)-Tyr(6)) (2), have been isolated from the methanol extract of the seeds of Annona reticulata. Their Structures were elucidated on the basis of the MS/MS fragmentation using a Q-TOF mass spectrometer equipped with an ESI Source, chemical degradation and extensive 2D-NMR. The solution conformation of cycloreticulin C involves two beta-turns, one of type II with trans-Pro(1) and Gly(2) at the corners, another of type VIa with trans-Pro(4) and cis-Pro(5) at the corners, and followed by a beta-bulge at the Tyr(6)-Val(7) level. The solid state and solution conformations of glabrin A have been analyzed by X-ray and 2D-NMR studies, respectively, and are characterized by the presence of two beta-turns, the first of type VIa and the second intermediary between types I and III at the solid state and a gamma-turn in solution. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.055