title: The identification of 5'-fluoro-5-deoxyinosine as a shunt product in cell free extracts of Streptomyces cattleya.
abstract: 5'-Fluoro-5'-deoxyinosine (5'-FDI) is identified as an adventitious side product that accumulates in cell free incubations of SAM and fluoride ion in Streptomyces cattleya. 5'-FDI was identified by a combination of isotopic labelling studies and co-synthesis studies as well as enzymatic degradation. Although it is an efficiently generated end product of the cell free incubations, 5'-FDI is not a biosynthetic intermediate and it does not accumulate as a fluorometabolite with fluoroacetate and 4-fluorothreonine in whole cell incubations of S. cattleya. Clearly the purine deaminase which converts 5'-fluoro-5'-deoxyadenosine (5'-FDA) to 5'-FDI in the cell free extract does not come into contact with 5'-FDA in whole cells, suggesting some level of compartmentalisation in cells of S. cattleya. The biotransformation of 5'-FDI from fluoride ion extends the range of organofluorine products, beyond biosynthetic intermediates, that can be generated by this system, for applications such as enzymatic labelling with fluorine-18 for positron emission tomography applications.
authors.affiliation: School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, St. Andrews, Fife, UK.
authors.forename: Steven L
authors.initials: SL
authors.lastname: Cobb
authors.forename: Hai
authors.initials: H
authors.lastname: Deng
authors.forename: John T G
authors.initials: JT
authors.lastname: Hamilton
authors.forename: Ryan P
authors.initials: RP
authors.lastname: McGlinchey
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
authors.forename: Christoph
authors.initials: C
authors.lastname: Schaffrath
mesh_terms: D001711:Biotransformation; D002474:Cell-Free System; D004121:Dimethyl Sulfoxide; D007288:Inosine / Q000031:analogs & derivatives* / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D013302:Streptomyces / Q000737:chemistry*
chemical_list: C507806:5'-fluoro-5-deoxyinosine; D007288:Inosine; D004121:Dimethyl Sulfoxide