Biosynthesis of antibiotics of the virginiamycin family, 5. The conversion of phenylalanine to phenylglycine in the biosynthesis of virginiamycin S1.

Conversion of L-phenylalanine to L-phenylglycine in the biosynthesis of virginiamycin S1 (1) can, in principle, take place with intramolecular nitrogen transfer or with intermolecular nitrogen transfer. A labeling experiment with DL-[3-13C, 15N]phenylalanine showed that the resulting L-phenylglycine contained no labeled nitrogen, indicating that the rearrangement proceeds via an intermolecular pathway.