Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 44, Pages 11314-11318Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803144
Keywords
bio-orthogonal catalysis; dehydroalanine; nisin; photoredox catalysis; thiostrepton
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Funding
- Netherlands Ministry of Education, Culture and Science [024.001.035]
- Netherlands Organisation for Scientific Research (NWO, vici grant) [724.013.003]
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Dehydroalanine (Dha) and dehydrobutyrine (Dhb) are remarkably versatile non-canonical amino acids often found in antimicrobial peptides. This work presents the selective modification of Dha and Dhb in antimicrobial peptides through photocatalytic activation of organoborates under the influence of visible light. Ir(dF(CF3)ppy)(2)(dtbbpy)PF6 was used as a photoredox catalyst in aqueous solutions for the modification of thiostrepton and nisin. The mild conditions and high selectivity for the dehydrated residues show that photoredox catalysis is a promising tool for the modification of peptide-derived natural products.
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