The identification of 5'-fluoro-5-deoxyinosine as a shunt product in cell free extracts of Streptomyces cattleya.
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.
Cobb
Steven L
SL
School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, St. Andrews, Fife, UK.
Deng
Hai
H
Hamilton
John T G
JT
McGlinchey
Ryan P
RP
O'Hagan
David
D
Schaffrath
Christoph
C
D001711:Biotransformation; D002474:Cell-Free System; D004121:Dimethyl Sulfoxide; D007288:Inosine / Q000031:analogs & derivatives* / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D013302:Streptomyces / Q000737:chemistry*
C507806:5'-fluoro-5-deoxyinosine; D007288:Inosine; D004121:Dimethyl Sulfoxide