THE BIOSYNTHESIS OF THE STREPTOMYCES ANTIBIOTIC BICYCLOMYCIN

Authors
BRADLEY EL HERBERT RB LAWRIE KWM KHAN JA MOODY CM YOUNG DW
Citation
El. Bradley et al., THE BIOSYNTHESIS OF THE STREPTOMYCES ANTIBIOTIC BICYCLOMYCIN, Tetrahedron letters, 37(38), 1996, pp. 6935-6938
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
38
Year of publication
1996
Pages
6935 - 6938
Database
ISI
SICI code
0040-4039(1996)37:38<6935:TBOTSA>2.0.ZU;2-T
Abstract
Bicyclomycin 5 is biosynthesized in Streptomyces sapporonensis from L- leucine 2 and L-isoleucine 1 by way of the naturally occurring diketop iperazine 3 and dihydrobicyclomycin 4. The mode of incorporation of (2 S,4R)-[5,5,5-H-2(3)]leucine into 5 (and 4) shows that the entry of the 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. Copyright (C) 1996 Elsev ier Science Ltd