hymenistatin 1 | 129536-23-8

• 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: hymenistatin 1
• 英文别名: hymenistatin；cyclo(-Pro-Pro-Tyr-Val-Pro-Leu-Ile-Ile)；Hymenistatin I；(1S,7S,10S,13S,19S,22S,25S,28S)-25,28-bis[(2S)-butan-2-yl]-10-[(4-hydroxyphenyl)methyl]-22-(2-methylpropyl)-13-propan-2-yl-3,9,12,15,21,24,27,30-octazatetracyclo[28.3.0.03,7.015,19]tritriacontane-2,8,11,14,20,23,26,29-octone
• CAS: 129536-23-8
• 化学式: C₄₇H₇₂N₈O₉
• 分子量: 893.137
• InChiKey: NACGNHONDBBQGE-MXKYYYADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  64
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  227
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Boc-Ile-Pro-Pro-Tyr-OH 在 N-甲基吗啉 、 吡啶 、 lithium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 218.0h， 生成 hymenistatin 1
  参考文献：
  名称：

  Synthetic studies on cyclic octapeptides: Yunnanin F and Hymenistatin

  摘要：

  Two biologically active cyclic peptides, Yunnanin F 8 and Hymenistatin 16 were synthesized and the structures were established on the basis of analytical, IR, NMR and mass spectral data. The newly synthesized compounds were screened for their antimicrobial and pharmacological activities. These cyclic octapeptides have shown moderate to good growth inhibition against bacterial strains and weak activity against fungal strains more than that of the standard drug against only Pseudoinonas aeruginosa but weak to moderate activity against remaining three bacterial strains. They have shown very weak activity against fungal strains. Yunnanin F possessed good anthelmintic activity while Hymenistatin possessed very low activity, but both showed moderate anti-inflammatory activity. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.013

文献信息

• Synthesis and Solvent Effects on the Conformation of Hymenistatin 1
  作者：Robert K. Konat、Dale F. Mierke、Horst Kessler、Bernhard Kutscher、Michael Bernd、Rainer Voegeli

  DOI：10.1002/hlca.19930760422

  日期：1993.6.30

  The cyclic octapeptide cyclo(-Pro-Pro-Tyr-Val-ProLeu-Ile-Ile-) (1), isolated from the Hymeniacidon sponge, was synthesized and examined conformationally using NMR and molecular-dynamics simulations. Most structural parameters of synthetic 1 are in accord with those reported for the isolated material. Our study indicates some small but significant differences in the assignment of the 1H- and 13C-NMR

  从海门酸海绵中分离的环状八肽环（-Pro-Pro-Tyr-Val-ProLeu-Ile-Ile-）（1）合成并使用NMR和分子动力学模拟进行构象检查。合成物1的大多数结构参数与所报道的分离材料一致。我们的研究表明，在1 H和13 C-NMR共振的赋值与天然物质的赋值中，存在一些细微但显着的差异。使用1确定CHCl3和DMSO中的构象H-NMR和分子动力学模拟。在模拟过程中，NOE和耦合常数均被用作实验约束，明确使用了与NMR研究相同的溶剂。检查了溶剂与1相互作用的差异，从而洞悉了所观察到的构象差异。显性构象包含分别在CHCl 3和DMSO中围绕Pro 1 -Pro 2顺式肽键的Ile 8 -Tyr 3的ßVIa转角和围绕Val 4 -Ile 7的βI或ßII转角。