NH₂-D-Dab-L-Dab-L-Dab-L-Leu-D-Phe-L-Dab-L-Dab-L-Leu-NH₂

• 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: NH₂-D-Dab-L-Dab-L-Dab-L-Leu-D-Phe-L-Dab-L-Dab-L-Leu-NH₂
• 英文别名: H₂N-D-Dab-Dab-Dab-Leu-D-Phe-Dab-Dab-Leu-NH₂；H-D-Dab-Dab-Dab-Leu-D-Phe-Dab-Dab-Leu-NH2；(2S)-2-[[(2S)-4-amino-2-[[(2S)-4-amino-2-[[(2R)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-4-amino-2-[[(2R)-2,4-diaminobutanoyl]amino]butanoyl]amino]butanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoyl]amino]butanoyl]amino]butanoyl]amino]-4-methylpentanamide
• 化学式: C₄₁H₇₄N₁₄O₈
• 分子量: 891.128
• InChiKey: ADSQSNBEQVNQSL-RVUVNBPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  63
• 可旋转键数：
  31
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  403
• 氢给体数：
  14
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  Fmoc-L-亮氨酸 、 Fmoc-L-苯丙氨酸 、 NAlpha-芴甲氧羰基-Nγ-羰-L-2,4-氨基丁酸 、 N-Alpha-(9-芴甲氧羰基)-N-β-叔丁氧羰基-D-2,4-二氨基丁酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.18h， 以77%的产率得到NH₂-D-Dab-L-Dab-L-Dab-L-Leu-D-Phe-L-Dab-L-Dab-L-Leu-NH₂
  参考文献：
  名称：

  “CLipP”ing on lipids to generate antibacterial lipopeptides

  摘要：

  我们在此报告了通过Cysteine Lipidation on a Peptide or Amino Acid (CLipPA)技术合成的环脂肽battacin的12个线性类似物的生物和计算评价结果。

  DOI：

  10.1039/d0sc01814g

文献信息

• Antimicrobial Peptides with Potential for Biofilm Eradication: Synthesis and Structure Activity Relationship Studies of Battacin Peptides
  作者：Gayan Heruka De Zoysa、Alan James Cameron、Veena V. Hegde、Srinivasarao Raghothama、Vijayalekshmi Sarojini

  DOI：10.1021/jm501084q

  日期：2015.1.22

  We report on the first chemical syntheses and structureactivity analyses of the cyclic lipopeptide battacin which revealed that conjugation of a shorter fatty acid, 4-methyl-hexanoic acid, and linearization of the peptide sequence improves antibacterial activity and reduces hemolysis of mouse blood cells. This surprising finding of higher potency in linear lipopeptides than their cyclic counterparts is economically beneficial. This novel lipopeptide was membrane lytic and exhibited antibiofilm activity against Pseudomonas aeruginosa, Staphylococcus aureus, and, for the first time, Pseudomonas syringe pv. actinidiae. The peptide was unstructured in aqueous buffer and dimyristoylphosphatidylcholine-polymerized diacetylene vesicles, with 12% helicity induced in 50% v/v of trifluoroethanol. Our results indicate that a well-defined secondary structure is not essential for the observed antibacterial activity of this novel lipopeptide. A truncated pentapeptide conjugated to 4-methyl hexanoic acid, having similar potency against Gram negative and Gram positive pathogens was identified through alanine scanning.