Structure of the major glycopeptide of the teicoplanin complex

The structure of the pseudoaglycon of the teicoplanin glycopeptides is described. The psi -aglycon has a peptide core that is identical with antibiotic A41030B, and N-acetylglucosamine is attached to the aglycon through the benzylic hydroxyl group at the A-1' position. The teicoplanin glycopeptides have a mannose moiety linked to the psi -aglycon through a phenol at D-5 and an N-acylglucosamine attached through the B-4 phenol; the acyl chain is variable, giving rise to the various members of the teicoplanin complex. The major teicoplanin glycopeptide has the composition C sub(88)H sub(97)N sub(9)O sub(33)Cl sub(2) (integral molecular weight = 1877). The structure elucidation is based on super(1)H NMR studies, FAB/MS studies, and the results of amino acid analysis.