Pep5: Structure Elucidation of a Large Lantibiotic

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Abstract
Lantibiotics are peptide antibiotics which contain lanthionine. Pep 5, a strongly basic compound, is produced from Staphylococcus epidermidis 5 by ribosomal synthesis of a precursor peptide and post‐translational modification. The antibiotic activity of Pep 5 rests on the formation of strain‐dependent pores in bacterial membranes. Pep 5 is the hitherto largest lantibiotic (Mr = 3488). It is N‐terminally blocked by a 2‐oxobutyryl residue and contains, besides 25 protein amino acids, dehydrobutyrine (2), meso‐lanthionine (2) and 3‐methyllanthionine (1). Automatic Edman degradation, mass spectrometry of enzymatically obtained fragments and chemical derivatization gave a 34‐peptide sequence with three sulfide rings (lanthionine = S(CH2CHNH2COOH)2).