title: Cylindrocyclophane biosynthesis involves functionalization of an unactivated carbon center.
abstract: The cylindrocyclophanes are a family of natural products that share a remarkable paracyclophane carbon scaffold. Using genome sequencing and bioinformatic analyses, we have discovered a biosynthetic gene cluster involved in the assembly of cylindrocyclophane F. Through a combination of in vitro enzyme characterization and feeding studies, we confirm the connection between this gene cluster and cylindrocyclophane production, elucidate the chemical events involved in initiating and terminating an unusual type I polyketide synthase assembly line, and discover that macrocycle assembly involves functionalization of an unactivated carbon center.
authors.affiliation: Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
authors.forename: Hitomi
authors.initials: H
authors.lastname: Nakamura
authors.forename: Hilary A
authors.initials: HA
authors.lastname: Hamer
authors.forename: Gopal
authors.initials: G
authors.lastname: Sirasani
authors.forename: Emily P
authors.initials: EP
authors.lastname: Balskus
mesh_terms: D002244:Carbon / Q000737:chemistry / Q000378:metabolism*; D019295:Computational Biology; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry / Q000378:metabolism*; D048630:Polyketide Synthases / Q000378:metabolism
chemical_list: D011084:Polycyclic Aromatic Hydrocarbons; C434088:cylindrocyclophane F; D002244:Carbon; D048630:Polyketide Synthases