cyclo(Val-Orn-Leu-D-2-Nal-Pro)2; 2-Nal = 2-naphthylalanine | 1110635-24-9

• 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: cyclo(Val-Orn-Leu-D-2-Nal-Pro)2; 2-Nal = 2-naphthylalanine
• 英文别名: cyclo[D-2Nal-Pro-Val-Orn-Leu-D-2Nal-Pro-Val-Orn-Leu]；(3R,6S,9S,12S,15S,21R,24S,27S,30S,33S)-9,27-bis(3-aminopropyl)-6,24-bis(2-methylpropyl)-3,21-bis(naphthalen-2-ylmethyl)-12,30-di(propan-2-yl)-1,4,7,10,13,19,22,25,28,31-decazatricyclo[31.3.0.015,19]hexatriacontane-2,5,8,11,14,20,23,26,29,32-decone
• CAS: 1110635-24-9
• 化学式: C₆₈H₉₆N₁₂O₁₀
• 分子量: 1241.58
• InChiKey: JGNGLHYUNJWHMG-VFHFZBNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  90
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  326
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  cyclo(Val-Orn(For)-Leu-D-2-Nal-Pro)2; 2-Nal = 2-naphthylalanine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 cyclo(Val-Orn-Leu-D-2-Nal-Pro)2; 2-Nal = 2-naphthylalanine
  参考文献：
  名称：

  Therapeutic Index of Gramicidin S is Strongly Modulated by d-Phenylalanine Analogues at the β-Turn

  摘要：

  Analogues of the cationic antimicrobial peptide gramicidin S (GS), cyclo(Val-Orn-Leu-D-Phe-Pro)(2), with D-Phe residues replaced by different (restricted mobility, mostly) surrogates have been synthesized and used in SAR studies against several pathogenic bacteria. While all D-Phe substitutions are shown by NMR to preserve the overall beta-sheet conformation, they entail subtle structural alterations that lead to significant modifications in biological activity. In particular, the analogue incorporating D-Tic (1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid) shows a modest but significant increase in therapeutic index, mostly due to a sharp decrease in hemolytic effect. The fact that NMR data show a shortened distance between the D-Tic aromatic ring and the Orn delta-amino group may help explain the improved antibiotic profile of this analogue.

  DOI：

  10.1021/jm800886n