N-α-Boc-L-His(2-cyclobutyl)-L-Arg-NHBzl | 1184963-06-1

• 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: N-α-Boc-L-His(2-cyclobutyl)-L-Arg-NHBzl
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-(benzylamino)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-(2-cyclobutyl-1H-imidazol-5-yl)-1-oxopropan-2-yl]carbamate
• CAS: 1184963-06-1
• 化学式: C₂₈H₄₂N₈O₄
• 分子量: 554.693
• InChiKey: VJNBJCNUNWJXQS-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  190
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-α-Boc-L-His(2-cyclobutyl)-L-Arg-NHBzl 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.25h， 以93%的产率得到L-His(2-cyclobutyl)-L-Arg-NHBzl dihydrochloride
  参考文献：
  名称：

  Discovery of Trp-His and His-Arg Analogues as New Structural Classes of Short Antimicrobial Peptides

  摘要：

  Naturally occurring antimicrobial peptides contain a large number of amino acid residues, which limits their clinical applicability. In search of short antimicrobial peptides, which represent a possible alternative for lead structures to fight antibiotic resistant microbial infections, a series of synthetic peptide analogues based oil Trp-His and His-Arg structural frameworks have been prepared and found to be active against several Gram-negative and Gram-positive bacterial strains as well as against a fungal strain with MIC values of the most potent Structures in the range of 5-20 mu g/mL ((IC50 in the range of 1-5 mu g/mL). The synthesized peptides showed no cytotoxic effect in an MTT assay up to the highest test concentration of 200 mu g/mL. A combination of small size, presence of unnatural amino acids, high antimicrobial activity, and absence of cytotoxicity reveals the synthesized Trp-His and His-Arg analogues as promising candidates for novel antimicrobial therapeutics.

  DOI：

  10.1021/jm900622d
• 作为产物：
  描述：

  (S)-2-((tert-butoxycarbonyl)amino)-3-(2-cyclobutyl-1H-imidazol-4-yl)propanoic acid 、 N1-benzyl-(2S)-2-amino-5-amino(imino)methylaminopentanamide 在 endo-N-hydroxy-5-norbornene-2,3-dicarboximide 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.08h， 以50%的产率得到N-α-Boc-L-His(2-cyclobutyl)-L-Arg-NHBzl
  参考文献：
  名称：

  Discovery of Trp-His and His-Arg Analogues as New Structural Classes of Short Antimicrobial Peptides

  摘要：

  Naturally occurring antimicrobial peptides contain a large number of amino acid residues, which limits their clinical applicability. In search of short antimicrobial peptides, which represent a possible alternative for lead structures to fight antibiotic resistant microbial infections, a series of synthetic peptide analogues based oil Trp-His and His-Arg structural frameworks have been prepared and found to be active against several Gram-negative and Gram-positive bacterial strains as well as against a fungal strain with MIC values of the most potent Structures in the range of 5-20 mu g/mL ((IC50 in the range of 1-5 mu g/mL). The synthesized peptides showed no cytotoxic effect in an MTT assay up to the highest test concentration of 200 mu g/mL. A combination of small size, presence of unnatural amino acids, high antimicrobial activity, and absence of cytotoxicity reveals the synthesized Trp-His and His-Arg analogues as promising candidates for novel antimicrobial therapeutics.

  DOI：

  10.1021/jm900622d

文献信息

• Discovery of Trp-His and His-Arg Analogues as New Structural Classes of Short Antimicrobial Peptides
  作者：Rohit K. Sharma、Ravi P. Reddy、Werner Tegge、Rahul Jain

  DOI：10.1021/jm900622d

  日期：2009.12.10

  Naturally occurring antimicrobial peptides contain a large number of amino acid residues, which limits their clinical applicability. In search of short antimicrobial peptides, which represent a possible alternative for lead structures to fight antibiotic resistant microbial infections, a series of synthetic peptide analogues based oil Trp-His and His-Arg structural frameworks have been prepared and found to be active against several Gram-negative and Gram-positive bacterial strains as well as against a fungal strain with MIC values of the most potent Structures in the range of 5-20 mu g/mL ((IC50 in the range of 1-5 mu g/mL). The synthesized peptides showed no cytotoxic effect in an MTT assay up to the highest test concentration of 200 mu g/mL. A combination of small size, presence of unnatural amino acids, high antimicrobial activity, and absence of cytotoxicity reveals the synthesized Trp-His and His-Arg analogues as promising candidates for novel antimicrobial therapeutics.