Biosynthesis of Antibiotics of the Virginiamycin Family. 8. Formation of the Dehydroproline Residue

Article abstract of DOI:10.1021/ja00197a064

The formation of the dehydroproline residue of the antibiotic virginiamycin M₁ occurs with equal facility from both (R)- and (S)-proline; the 3-pro-R proton of proline is lost stereospecifically in this process. cis-3-Hydroxyproline but not trans-3-hydroxyproline is incorporated into the antibiotic, although less efficiently than proline, and virginiamycin M₂ is converted into virginiamycin M₁.These results suggest that virginiamycin M₁ is most probably formed by incorporation of (S)-proline into virginiamycin M₂, which then undergoes hydroxylation withretention of configuration and elimination of water to yield virginiamycin M₁.