Source:http://linkedlifedata.com/resource/pubmed/id/17574646
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
5
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pubmed:dateCreated |
2007-8-28
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pubmed:abstractText |
(3R,4S)-5-Fluoro-5-deoxy-D-ribulose-1-phosphate (5-FDRulP) has been identified as the third fluorinated intermediate on the biosynthetic pathway to fluoroacetate and 4-fluorothreonine in Streptomyces cattleya. 5-FDRulP is generated after formation of 5'-fluoro-5'-deoxyadenosine (5'-FDA) and then phosphorolysis of 5'-FDA to 5-fluoro-5-deoxy-D-ribose-1-phosphate (5-FDRP) by the action of a purine nucleoside phosphorylase. An isomerase mediates the conversion of 5-FDRP to 5-FDRulP. The identity of the (3R,4S) diastereoisomer of 5-FDRulP was established by comparative (19)F{(1)H} NMR studies whereby 5-FDRulP that accumulated in a cell free extract of S. cattleya, was treated with a phytase to generate the non-phosphorylated sugar, 5-fluoro-5-deoxy-D-ribulose (5-FDRul). This S. cattleya product was compared to the product of an in-vitro biotransformation where separately 5-fluoro-5-deoxy-D-ribose and 5-fluoro-5-deoxy-D-xylose were converted to 5-fluoro-5-deoxy-D-ribulose and 5-fluoro-5-deoxy-D-xylulose respectively by the action of glucose isomerase. It was demonstrated that 5-fluoro-5-deoxy-D-ribose gave the identical diastereoisomer to that observed from 5-FDRulP.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/1-fluoro-1-deoxyribulose-5-phosphate,
http://linkedlifedata.com/resource/pubmed/chemical/Aldose-Ketose Isomerases,
http://linkedlifedata.com/resource/pubmed/chemical/Bacterial Proteins,
http://linkedlifedata.com/resource/pubmed/chemical/Fluoroacetates,
http://linkedlifedata.com/resource/pubmed/chemical/Oxidoreductases,
http://linkedlifedata.com/resource/pubmed/chemical/Phosphorylases,
http://linkedlifedata.com/resource/pubmed/chemical/Protein Isoforms,
http://linkedlifedata.com/resource/pubmed/chemical/Ribulosephosphates,
http://linkedlifedata.com/resource/pubmed/chemical/fluorinase,
http://linkedlifedata.com/resource/pubmed/chemical/xylose isomerase
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pubmed:status |
MEDLINE
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pubmed:month |
Oct
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pubmed:issn |
0045-2068
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
35
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
375-85
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pubmed:dateRevised |
2011-11-17
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pubmed:meshHeading |
pubmed-meshheading:17574646-Aldose-Ketose Isomerases,
pubmed-meshheading:17574646-Bacterial Proteins,
pubmed-meshheading:17574646-Biosynthetic Pathways,
pubmed-meshheading:17574646-Catalysis,
pubmed-meshheading:17574646-Cell-Free System,
pubmed-meshheading:17574646-Fluoroacetates,
pubmed-meshheading:17574646-Gas Chromatography-Mass Spectrometry,
pubmed-meshheading:17574646-Magnetic Resonance Spectroscopy,
pubmed-meshheading:17574646-Models, Chemical,
pubmed-meshheading:17574646-Oxidoreductases,
pubmed-meshheading:17574646-Phosphorylases,
pubmed-meshheading:17574646-Protein Isoforms,
pubmed-meshheading:17574646-Ribulosephosphates,
pubmed-meshheading:17574646-Streptomyces
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pubmed:year |
2007
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pubmed:articleTitle |
The identification of (3R,4S)-5-fluoro-5-deoxy-D-ribulose-1-phosphate as an intermediate in fluorometabolite biosynthesis in Streptomyces cattleya.
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pubmed:affiliation |
School of Chemistry and Centre for Biomolecular Science, University of St Andrews, North Haugh, St Andrews KY16 9ST, UK.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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