Tetrahedron Letters p. 6935 - 6938 (1996)
Update date:2022-08-11
Topics:
Bradley, Emma L.
Herbert, Richard B.
Lawrie, Kenneth W.M.
Khan, Jeffrey A.
Moody, Claire M.
Young, Douglas W.
Bicyclomycin 5 is biosynthesized in Streptomyces sapporonensis from L-leucine 2 and L-isoleucine 1 by way of the naturally occurring diketopiperazine 3 and dihydrobicyclomycin 4. The mode of incorporation of (2S,4R)-[5,5,5-2H3]leucine into 5 (and 4) shows that the entry of hydroxy group at C-2' occurs with unusual inversion of configuration. The results of inhibition studies permit a useful working hypothesis to be advanced for bicyclomycin biosynthesis.
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