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Pentaminomycins F and G, First Non-Ribosomal Peptides Containing 2-Pyridylalanine
preprintsubmitted on 26.10.2020, 12:11 and posted on 09.11.2020, 20:42 by Daniel Carretero-Molina, Francisco Javier Ortiz-Lopez, Jesús Martín, Ignacio González, Marina Sánchez-Hidalgo, Fernando Román-Hurtado, Caridad Díaz, Mercedes de la Cruz, Olga Genilloud, Fernando Reyes
Pentaminomycins F-H, a group of three new hydroxyarginine-containing cyclic pentapeptides, were isolated from cultures of a Streptomyces cacaoi subsp. cacaoi strain along with the known pentaminomycins A-E. The structures of the new peptides were determined by a combination of mass spectrometry and NMR and Marfey's analyses. Among them, pentaminomycins F and G were shown to contain in their structures the rare amino acid 3-(2-pyridyl)-alanine. This finding represents the first reported example of non-ribosomal peptides containing this residue. The LDLLD chiral sequence found for the three compounds was in agreement with that reported for previously isolated pentaminomycins and consistent with the epimerization domains present in the putative non-robosomal peptide synthetase (NRPS) biosynthetic gene cluster.