(ACHC-ACHC-β³Lys)3 | 1610960-64-9

• 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: (ACHC-ACHC-β³Lys)3
• 英文别名: (1S,2S)-2-amino-N-[(1S,2S)-2-[[(1S)-5-amino-1-[2-[[(1S,2S)-2-[[(1S,2S)-2-[[(1S)-5-amino-1-[2-[[(1S,2S)-2-[[(1S,2S)-2-[[(1S)-5-amino-1-(2-amino-2-oxo-ethyl)pentyl]carbamoyl]cyclohexyl]carbamoyl]cyclohexyl]amino]-2-oxo-ethyl]pentyl]carbamoyl]cyclohexyl]carbamoyl]cyclohexyl]amino]-2-oxo-ethyl]pentyl]carbamoyl]cyclohexyl]cyclohexanecarboxamide；(1S,2S)-2-amino-N-[(1S,2S)-2-[[(3S)-7-amino-1-[[(1S,2S)-2-[[(1S,2S)-2-[[(3S)-7-amino-1-[[(1S,2S)-2-[[(1S,2S)-2-[[(3S)-1,7-diamino-1-oxoheptan-3-yl]carbamoyl]cyclohexyl]carbamoyl]cyclohexyl]amino]-1-oxoheptan-3-yl]carbamoyl]cyclohexyl]carbamoyl]cyclohexyl]amino]-1-oxoheptan-3-yl]carbamoyl]cyclohexyl]cyclohexane-1-carboxamide
• CAS: 1610960-64-9
• 化学式: C₆₃H₁₁₁N₁₃O₉
• 分子量: 1194.66
• InChiKey: NHOUKXIINRDZRI-YTFPMBQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  85
• 可旋转键数：
  32
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  380
• 氢给体数：
  13
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  NΒ-芴甲氧羰基-NΩ-叔丁氧羰基-L-Β-高赖氨酸 、 N-芴甲氧羰基-(1S,2S)-2-氨基环己烷羧酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.3h， 生成 (ACHC-ACHC-β³Lys)3
  参考文献：
  名称：

  Hydrophobicity and Helicity Regulate the Antifungal Activity of 14-Helical β-Peptides

  摘要：

  Candida albicans is one of the most prevalent fungal pathogens, causing both mucosal candidiasis and invasive candidemia. Antimicrobial peptides (AMPs), part of the human innate immune system, have been shown to exhibit antifungal activity but have not been effective as pharmaceuticals because of low activity and selectivity in physiologically relevant environments. Nevertheless, studies on a-peptide AMPs have revealed key features that can be designed into more stable structures, such as the 14-helix of beta-peptide-based oligomers. Here, we report on the ways in which two of those features, hydrophobicity and helicity, govern the activity and selectivity of 14-helical beta-peptides against C. albicans and human red Hood cells. Our results reveal both antifungal activity and hemolysis to correlate to hydrophobicity, with intermediate levels of hydrophobicity leading to high antifungal activity and high selectivity toward C. albicans. Helical structure-forming propensity further influenced this window of selective antifungal activity, with more stable helical structures eliciting specificity for C. albicans over a broader range of hydrophobicity. Our findings also reveal cooperativity between hydrophobicity and helicity in regulating antifungal activity and specificity. The results of this study provide critical insight into the ways in which hydrophobicity and helicity govern the activity and specificity of AMPs and identify criteria that may be useful for the design of potent and selective antifungal agents.

  DOI：

  10.1021/cb500203e