ASSOCIATION OF 6-OXO-PIPERIDINE-2-CARBOXYLIC ACID WITH PENICILLIN V: PRODUCTION IN PENICILLIUM CHRYSOGENUM FERMENTATIONS

ASSOCIATION OF 6-OXO-PIPERIDINE-2-CARBOXYLIC ACID WITH PENICILLIN V: PRODUCTION IN PENICILLIUM CHRYSOGENUM FERMENTATIONS

Analysis of a 13C NMR spectrum of a concentrated broth from Penicillium chrysogenum fermentation revealed the presence of penicillin V and 6-oxo-piperidine-2-carboxylic acid (1) as the principal constituents. The latter lactam, identical to an authentic sample prepared by the cyclization of α-aminoa...

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Veröffentlicht in:Journal of antibiotics 1980, Vol.33(11), pp.1348-1351
Hauptverfasser: BRUNDIDGE, STEVEN P., GAETA, FEDERICO C. A., HOOK, DEREK J., SAPINO, CHESTER, Jr, ELANDER, RICHARD P., MORIN, ROBERT B.
Format: Artikel
Sprache:eng
Schlagworte:
Carbon Radioisotopes
Culture Media - analysis
Fermentation
Lactams - analysis
Lactams - biosynthesis
Lactams - isolation & purification
Magnetic Resonance Spectroscopy
Penicillin V - analysis
Penicillin V - biosynthesis
Penicillin V - isolation & purification
Penicillium - metabolism
Penicillium chrysogenum - metabolism
Pipecolic Acids
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Zusammenfassung:Analysis of a 13C NMR spectrum of a concentrated broth from Penicillium chrysogenum fermentation revealed the presence of penicillin V and 6-oxo-piperidine-2-carboxylic acid (1) as the principal constituents. The latter lactam, identical to an authentic sample prepared by the cyclization of α-aminoadipic acid was present to the extent of 28mol% of penicillin V. The lactam isolated from the broth was nearly racemic, having a slight excess of the L-isomer. This isolation provides further evidence regarding the biosynthetic precursors of the hydrophobic penicillins.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.33.1348