Biosynthetic studies of the glycopeptide teicoplanin by (1)H and (13)C 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-(13)C]glucose or 9.7% [U-(13)C]glucose. The fractional enrichment pattern of teicoplanin produced in the medium containing [1-(13)C]glucose was obtained from a one-dimensional (13)C 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-(13)C]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.
Heydorn
A
A
Center for Process Biotechnology, Department of Biotechnology, Technical University of Denmark, DK-2800 Lyngby, Denmark.
Petersen
B O
BO
Duus
J O
JO
Bergmann
S
S
Suhr-Jessen
T
T
Nielsen
J
J
D000192:Actinomycetales / Q000737:chemistry / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000737:chemistry; D002247:Carbon Isotopes; D005947:Glucose / Q000378:metabolism; D005998:Glycine / Q000031:analogs & derivatives; D006601:Hexoses / Q000032:analysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017334:Teicoplanin / Q000096:biosynthesis* / Q000737:chemistry; D014443:Tyrosine / Q000378:metabolism
D000900:Anti-Bacterial Agents; D002247:Carbon Isotopes; D006601:Hexoses; D014443:Tyrosine; D017334:Teicoplanin; D005947:Glucose; D005998:Glycine