Biosynthetic studies of the glycopeptide teicoplanin by 1H and 13C NMR

The biosynthesis of the glycopeptide antibiotic teicoplanin was studied by growing a teicoplanin producing strain of Actinoplanes teichomyceticus (ATCC 31121) on glucose containing either 34.0% [1-C-13]glucose or 9.7% [U-C-13]glucose. The fractional enrichment pattern of teicoplanin produced in the medium containing [1-C-13]glucose was obtained from a one-dimensional C-13 spectrum. The enrichment pattern showed characteristic peaks indicating that amino acids 3 and 7 are derived from acetate, whereas amino acids 1, 2, 4, 5, and 6 are derived from tyrosine, Multiplet structures in heteronuclear single quantum coherence spectra of teicoplanin produced in the medium containing [U-C-13]glucose showed characteristic coupling patterns supporting these results. Fractional enrichment patterns and multiplet structures of the three sugars in teicoplanin showed that about 50% of the sugars have the same labeling pattern as the glucose substrate whereas the rest have a labeling pattern showing that they are reassembled, probably from precursors in the primary metabolism.