KSRIVPAIPVSLL | 540741-29-5

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: KSRIVPAIPVSLL
• 英文别名: KSRIVPAIPVSLL-NH₂；Idr1；H-Lys-Ser-Arg-Ile-Val-Pro-Ala-Ile-Pro-Val-Ser-Leu-Leu-OH；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2,6-diaminohexanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-methylpentanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]propanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoic acid
• CAS: 540741-29-5
• 化学式: C₆₅H₁₁₇N₁₇O₁₆
• 分子量: 1392.75
• InChiKey: FVIDCRSQQHLAAS-OLAWGTLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  98
• 可旋转键数：
  43
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  526
• 氢给体数：
  17
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 Fmoc-L-脯氨酸 、 FMOC-O-叔丁基-L-丝氨酸 、 Fmoc-L-异亮氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-Pbf-L-精氨酸 在 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 、 N,N-二甲基乙酰胺 为溶剂， 反应 1.25h， 以16%的产率得到KSRIVPAIPVSLL
  参考文献：
  名称：

  Identification of New Nitric Oxide-Donating Peptides with Dual Biofilm Eradication and Antibacterial Activities for Intervention of Device-Related Infections

  摘要：

  Implantable medical device-related infections with biofilms have become a significant challenge in clinics. Based on the potential bacteria biofilm dispersing effect of nitric oxide (NO) and the unique antibacterial activity of antimicrobial peptides (AMP), we synthesized five peptides and selected the most potent one to conjugate its N-terminal with a furoxan moiety to offer a hitherto unknown NO-donating antimicrobial peptide (FOTyr-AMP), which exhibited Staphylococcus aureus and Escherichia coli biofilm dispersion and eradication, and potent antibacterial activities in vitro. In an implanted biofilm infection mice model, topical subcutaneous injection of FOTyr-AMP allowed synergetic eradication of bacterial biofilms and potent antibacterial activity, superior to the antibiotic cephalosporin C. Given the low hemolysis effect, little influence on the blood pressure, and potent in vivo efficacy of FOTyr-AMP, it is clear that subcutaneous administration of FOTyr-AMP could be a promising approach for the intervention of medical device-related biofilm infections with desirable safety.

  DOI：

  10.1021/acs.jmedchem.9b01832