Biosynthesis of the Antibiotic Obafluorin from p-Aminophenylalanine and Glycine (Glyoxylate)
Results of experiments using 'resting' cells of Pseudomonas fluorescens with -, - and 2H2>-glycine as precursors show that glyoxylic acid is specifically the source of C-1 and C-2 of the antibiotic obafluorin 1.The 13C labelling patterns are consistent with the passage of the precursors through the tartronic semialdehyde and glyoxylate pathways.The glycine derivative 6 is not a precursor for 1.The analogues 24 and 25 of p-aminophenylalanine 3 are synthesised and tested as substrates for biosynthesis in P. fluorescens.With 24, the metabolite 26 is detected; no metabolites of 25 are detected.
Certain 7-acylamido-3-(1-carboxy-loweralkyl-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids and their salts and easily hydrolyzed esters of the 4-carboxyl group were synthesized and found to be potent antibacterial agents which exhibited good aqueous solubility. In a preferred embodiment the 7-substituent was 2'-aminomethylphenylacetamido.
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(2008/06/13)
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