Biosynthesis of the streptovaricins: 3-amino-5-hydroxybenzoic acid as a precursor to the meta-C7N unit.
[Carboxy-14C]-3-amino-5-hydroxybenzoic acid (AHBA) has been shown to be incorporated by Streptomyces spectabilis to the extent of greater than 0.1% (35: 1 dilution) in the ansamycin antibiotic streptovaricin C, the major component of the streptovaricin complex. When [carboxy-13C]AHBA was similarly administered, C-21 (quinone methide carbonyl at 188.3 ppm) of streptovaricin C was specifically labeled (at twenty one times natural abundance). In preparation for the 13C incorporation study the 13C NMR spectrum of streptovaricin C was investigated, making extensive use of short- and long-range HETCOR. These assignments revise some of those proposed earlier for streptovaricin C.
Staley
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AL
Roger Adams Laboratory, University of Illinois, Urbana-Champaign 61801.
Rinehart
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KL
D062365:Aminobenzoates / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D002855:Chromatography, Thin Layer; D062385:Hydroxybenzoates; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D013302:Streptomyces / Q000378:metabolism*; D013310:Streptovaricin / Q000096:biosynthesis* / Q000737:chemistry / Q000031:analogs & derivatives
D062365:Aminobenzoates; D062385:Hydroxybenzoates; D013310:Streptovaricin; C031509:3-amino-5-hydroxybenzoic acid; C068094:streptovaricin C