Abstract
Efrapeptins are a group of microheterogeneous polypeptide antibiotics produced by the fungus Tolypocladium niveum, which are potent inhibitors of mitochondrial F1-ATPase. Efrapeptins contain an unusual 1,5-diazabicyclo[4:3:0]nonene (DBN) residue at the C-terminus. This study is driven by the hypothesis that the DBN residue could, in principle, arise by oxidative cyclization of a spermidine moiety. Electrospray ionization mass spectrometry of the peptide antibiotics 'elvapeptins' from T niveum establishes the presence of a C-terminal spermidine residue. Conversion of elvapeptins to efrapeptins by CuCl/pyridine demonstrates the transformation of the spermidine residue to the 1,5-diazabicyclo[4:3:0]nonene system by oxidative cyclization.
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More From: The journal of peptide research : official journal of the American Peptide Society
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