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.
D055598:Chemical Phenomena; D002621:Chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000096:biosynthesis; D013058:Mass Spectrometry; D010649:Phenylalanine / Q000378:metabolism*; D013302:Streptomyces / Q000378:metabolism*; D014769:Virginiamycin / Q000032:analysis / Q000096:biosynthesis*
D014769:Virginiamycin; D010649:Phenylalanine; C008852:2-phenylglycine; D005998:Glycine