title: Preparation of erythromycin analogs having functional groups at C-15.
abstract: Chemobiosynthesis has been used to prepare analogs of erythromycins having unique functional groups at the 15-position. Using diketide thioester feeding to genetically engineered Streptomyces coelicolor, analogs of 6-deoxyerythronolide B were prepared having 15-fluoro, 15-chloro, and 15-azido groups. Bioconversion using a genetically engineered mutant of Saccharopolyspora erythraea was used to produce 15-fluoroerythromycin A and 15-azidoerythromycin A. These new erythromycin analogs provide antibacterial macrolides with unique physicochemical properties and functional groups that allow for selective derivatization.
authors.affiliation: Kosan Biosciences, Inc., 3832, Bay Center Place, Hayward, California 94545, USA. Ashley@kosan.com
authors.forename: Gary W
authors.initials: GW
authors.lastname: Ashley
authors.forename: Mark
authors.initials: M
authors.lastname: Burlingame
authors.forename: Ruchir
authors.initials: R
authors.lastname: Desai
authors.forename: Hong
authors.initials: H
authors.lastname: Fu
authors.forename: Tim
authors.initials: T
authors.lastname: Leaf
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Licari
authors.forename: Chau
authors.initials: C
authors.lastname: Tran
authors.forename: Darren
authors.initials: D
authors.lastname: Abbanat
authors.forename: Karen
authors.initials: K
authors.lastname: Bush
authors.forename: Mark
authors.initials: M
authors.lastname: Macielag
mesh_terms: D004917:Erythromycin / Q000031:analogs & derivatives* / Q000096:biosynthesis* / Q000737:chemistry; D005818:Genetic Engineering; D015394:Molecular Structure; D048372:Streptomyces coelicolor / Q000235:genetics / Q000378:metabolism
chemical_list: C514531:15-azidoerythromycin A; C514530:15-fluoroerythromycin A; D004917:Erythromycin