Conversion of C14-and cis-or trans-4-H3-L-proline to 4-hydroxy-L-proline and 4-oxo-L-proline by Streptomyces antibioticus.

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Abstract
C14- and 4-cis or trans-H3-L-proline were administered to Streptomyces antibioticus during actinomycin synthesis. There was complete retention of the tritium label in hydroxyproline but a loss of the tritium label in oxoproline when cis-4-H3-proline was used as precursor; by contrast, an almost complete loss of the tritium label in both hydroxyproline and oxoproline was observed using trans -4 -H3-proline. Conversion of proline to hydroxyproline involves a displace?ment of the trans hydrogen with complete retention of configuration at carb?n atom 4 and that 4-oxoproline is not an intermediate in the reaction.