Document Detail


The identification of 5'-fluoro-5-deoxyinosine as a shunt product in cell free extracts of Streptomyces cattleya.
MedLine Citation:
PMID:  16165185     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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:
Steven L Cobb; Hai Deng; John T G Hamilton; Ryan P McGlinchey; David O'Hagan; Christoph Schaffrath
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioorganic chemistry     Volume:  33     ISSN:  0045-2068     ISO Abbreviation:  Bioorg. Chem.     Publication Date:  2005 Oct 
Date Detail:
Created Date:  2005-10-03     Completed Date:  2006-02-16     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  1303703     Medline TA:  Bioorg Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  393-401     Citation Subset:  IM    
Affiliation:
School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, St. Andrews, Fife, UK.
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MeSH Terms
Descriptor/Qualifier:
Biotransformation
Cell-Free System
Dimethyl Sulfoxide
Inosine / analogs & derivatives*,  analysis*
Magnetic Resonance Spectroscopy
Streptomyces / chemistry*
Chemical
Reg. No./Substance:
0/5'-fluoro-5-deoxyinosine; 58-63-9/Inosine; 67-68-5/Dimethyl Sulfoxide

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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