Isolation and identification of 3-propylidene-.DELTA.1-pyrroline-5-carboxylic acid, a biosynthetic precursor of lincomycin.

The Journal of Antibiotics
1992.0

Abstract

An accumulated lincomycin intermediate in UC 8292, a lincomycin nonproducing strain of Streptomyces lincolnensis, has been isolated and purified by employing an assay system based on complementation of UC 11066, another lincomycin nonproducing strain of S. lincolnensis. The structure of the purified intermediate is shown to be 3-propylidene-delta 1-pyrroline-5-carboxylic acid, or 1, 2, 3, 6-tetradehydro-propylproline by mass spectrometry and NMR spectroscopic studies. Based on the structure of this newly found intermediate, a biosynthetic pathway for propylproline is proposed as tyrosine-->L-3-hydroxytyrosine (Dopa)-->-->-->-->3-propylidene-delta 1-pyrroline-5-carboxylic acid-->3-propyl-delta 2-pyrroline-5-carboxylic acid-->propylproline.

Knowledge Graph

Similar Paper

Isolation and identification of 3-propylidene-.DELTA.1-pyrroline-5-carboxylic acid, a biosynthetic precursor of lincomycin.
The Journal of Antibiotics 1992.0
Isolation and identification of 3-propylidene-.DELTA.1-pyrroline-5-carboxylic acid, a biosynthetic precursor of lincomycin.
The Journal of Antibiotics 1992.0
Mutasynthesis of Lincomycin Derivatives with Activity against Drug-Resistant Staphylococci
Antimicrobial Agents and Chemotherapy 2010.0
Isolation and identification of 7,8-didemethyl-8-hydroxy-5-deazariboflavin, an unusual cosynthetic factor in streptomycetes, from Streptomyces lincolnensis.
The Journal of Antibiotics 1989.0
Co-overexpression of <i>lmbW</i> and <i>metK</i> led to increased lincomycin A production and decreased byproduct lincomycin B content in an industrial strain of <i>Streptomyces lincolnensis</i>
Journal of Applied Microbiology 2015.0
The identification of three new biosynthetic intermediates and one further biosynthetic enzyme in the clavulanic acid pathway
Journal of the Chemical Society, Chemical Communications 1993.0
Stoffwechselprodukte von Mikroorganismen. 232. Mitteilung. (<i>E</i>)‐3‐(1<i>H</i>‐Pyrrol‐3‐yl)‐2‐propensäure und (<i>E</i>)‐3‐(1<i>H</i>‐Pyrrol‐3‐yl)‐2‐propensäureamid aus <i>Streptomyces parvulus</i>, Stamm Tü 2480
Helvetica Chimica Acta 1985.0
The biosynthesis of pramanicin: origin of the carbon skeleton
Chemical Communications 1998.0
Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic 11-demethyltomaymycin and its biologically inactive metabolite oxotomaymycin by Streptomyces achromogenes
Biochemistry 1976.0
Pyrrolo[1,4]benzodiazepine antibiotics. Biosynthesis of the antitumor antibiotic 11-demethyltomaymycin and its biologically inactive metabolite oxotomaymycin by Streptomyces achromogenes
Biochemistry 1976.0