Origin of nitrogen in the biosynthesis of carbamoylpolyoxamic acid.
The biosynthetic origin of the carbamoylpolyoxamic sidechain of the polyoxin nucleoside peptide antibiotics was studied using 15N labeled alpha-amino-S-hydroxyvaleric acid as precursor. Gas chromatography mass spectrometry of polyoxamic acid isolated from culture filtrates of Streptomyces cacaoi var. asoensis showed incorporation of the nitrogen atom of alpha-amino-S-hydroxyvaleric acid into carbamoylpolyoxamic acid with an isotopic dilution factor of 23, thus establishing the intermediacy of alpha-amino-S-hydroxyvaleric acid and determination of the full biosynthetic pathway.
D000596:Amino Acids / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D002219:Carbamates / Q000378:metabolism; D006880:Hydroxy Acids / Q000378:metabolism; D009584:Nitrogen / Q000378:metabolism; D010072:Oxamic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D013302:Streptomyces / Q000378:metabolism*; D014631:Valerates / Q000378:metabolism
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D002219:Carbamates; D006880:Hydroxy Acids; D014631:Valerates; D009584:Nitrogen; D010072:Oxamic Acid