New aminocoumarin antibiotics derived from 4-hydroxycinnamic acid are formed after heterologous expression of a modified clorobiocin biosynthetic gene cluster.
Three new aminocoumarin antibiotics, termed ferulobiocin, 3-chlorocoumarobiocin and 8'-dechloro-3-chlorocoumarobiocin, were isolated from the culture broth of a Streptomyces coelicolor M512 strain expressing a modified clorobiocin biosynthetic gene cluster. Structural analysis showed that these new aminocoumarins were very similar to clorobiocin, with a substituted 4-hydroxycinnamoyl moieties instead of the prenylated 4-hydroxybenzoyl moiety of clorobiocin. The possible biosynthetic origin of these moieties is discussed.
Anderle
Christine
C
Pharmazeutisches Institut, Eberhard-Karls-Universität Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.
Li
Shu-Ming
SM
Kammerer
Bernd
B
Gust
Bertolt
B
Heide
Lutz
L
D049933:Aminocoumarins / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000737:chemistry / Q000302:isolation & purification; D003373:Coumaric Acids / Q000378:metabolism*; D003470:Culture Media / Q000378:metabolism; D015870:Gene Expression; D005798:Genes, Bacterial / Q000235:genetics*; D008826:Microbial Sensitivity Tests; D005810:Multigene Family / Q000235:genetics*; D009675:Novobiocin / Q000031:analogs & derivatives* / Q000096:biosynthesis; D011422:Propionates; D048372:Streptomyces coelicolor / Q000235:genetics* / Q000254:growth & development / Q000378:metabolism*