Journal of the American Chemical Society p. 5931 - 5935 (1989)
Update date:2022-07-29
Topics:
Purvis, Michael B.
LeFevre, Joseph W.
Jones, Vickie L.
Kingston, David G. I.
Biot, Andre M.
Gossele, Francis
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.
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