天然抗菌肽中脱水氨基酸的选择性氮杂迈克尔加成反应。
Selective Aza-Michael Addition to Dehydrated Amino Acids in Natural Antimicrobial Peptides.
机构信息
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747AG, Groningen, The Netherlands.
Department of Molecular Genetics, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 7, 9747AG, Groningen, The Netherlands.
出版信息
Chembiochem. 2024 Apr 2;25(7):e202400043. doi: 10.1002/cbic.202400043. Epub 2024 Feb 28.
We report the efficient and site selective modification of non-canonical dehydroamino acids in ribosomally synthesized and post-transationally modified peptides (RiPPs) by β-amination. The singly modified thiopeptide Thiostrepton showed an up to 35-fold increase in water solubility, and minimum inhibitory concentration (MIC) assays showed that antimicrobial activity remained good, albeit lower than the unmodified peptide. Also the lanthipeptide nisin could be modified using this method.
我们报告了通过β-氨化反应高效且选择性地对核糖体合成和翻译后修饰的肽（RiPPs）中的非典型脱氨氨基酸进行修饰。单修饰的硫肽硫链丝菌素（Thiostrepton）的水溶性提高了 35 倍，最小抑菌浓度（MIC）测定表明，其抗菌活性仍然良好，尽管低于未修饰的肽。此外，这种方法还可以修饰类杆菌肽 nisin。
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