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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
2
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pubmed:dateCreated |
1973-10-11
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pubmed:abstractText |
1. A method was developed for synthesizing UDP-apiose [uridine 5'-(alpha-d-apio-d-furanosyl pyrophosphate)] from UDP-glucuronic acid [uridine 5'-(alpha-d-glucopyranosyluronic acid pyrophosphate)] in 62% yield with the enzyme UDP-glucuronic acid cyclase. 2. UDP-apiose had the same mobility as uridine 5'-(alpha-d-xylopyranosyl pyrophosphate) when chromatographed on paper and when subjected to paper electrophoresis at pH5.8. When [(3)H]UDP-[U-(14)C]glucuronic acid was used as the substrate for UDP-glucuronic acid cyclase, the (3)H/(14)C ratio in the reaction product was that expected if d-apiose remained attached to the uridine. In separate experiments doubly labelled reaction product was: (a) hydrolysed at pH2 and 100 degrees C for 15min; (b) degraded at pH8.0 and 100 degrees C for 3min; (c) used as a substrate in the enzymic synthesis of [(14)C]apiin. In each type of experiment the reaction products were isolated and identified and were found to be those expected if [(3)H]UDP-[U-(14)C]apiose was the starting compound. 3. Chemical characterization established that the product containing d-[U-(14)C]apiose and phosphate formed on alkaline degradation of UDP-[U-(14)C]apiose was alpha-d-[U-(14)C]apio-d-furanosyl 1:2-cyclic phosphate. 4. Chemical characterization also established that the product containing d-[U-(14)C]apiose and phosphate formed on acid hydrolysis of alpha-d-[U-(14)C]apio-d-furanosyl 1:2-cyclic phosphate was d-[U-(14)C]apiose 2-phosphate. 5. The half-life periods for the degradation of UDP-[U-(14)C]apiose to alpha-d-[U-(14)C]apio-d-furanosyl 1:2-cyclic phosphate and UMP at pH8.0 and 80 degrees C, at pH8.0 and 25 degrees C and at pH8.0 and 4 degrees C were 31.6s, 97.2min and 16.5h respectively. The half-life period for the hydrolysis of UDP-[U-(14)C]-apiose to d-[U-(14)C]apiose and UDP at pH3.0 and 40 degrees C was 4.67min. After 20 days at pH6.2-6.6 and 4 degrees C, 17% of the starting UDP-[U-(14)C]apiose was degraded to alpha-d-[U-(14)C]apio-d-furanosyl 1:2-cyclic phosphate and UMP and 23% was hydrolysed to d-[U-(14)C]apiose and UDP. After 120 days at pH6.4 and -20 degrees C 2% of the starting UDP-[U-(14)C]apiose was degraded and 4% was hydrolysed.
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pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-12977745,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-13641241,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-13794843,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-14272320,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-14907728,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-4287931,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-4311783,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-4314545,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-4393018,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-4953927,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-5124813,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-5418465,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-5419754,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-5484469,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-5737946,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-5767313,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-5856607,
http://linkedlifedata.com/resource/pubmed/commentcorrection/4723773-5959418
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Jun
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pubmed:issn |
0264-6021
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:volume |
133
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
227-41
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pubmed:dateRevised |
2009-11-18
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pubmed:meshHeading |
pubmed-meshheading:4723773-Carbon Isotopes,
pubmed-meshheading:4723773-Carboxy-Lyases,
pubmed-meshheading:4723773-Chromatography, Ion Exchange,
pubmed-meshheading:4723773-Chromatography, Paper,
pubmed-meshheading:4723773-Drug Stability,
pubmed-meshheading:4723773-Electrophoresis, Paper,
pubmed-meshheading:4723773-Glucuronates,
pubmed-meshheading:4723773-Half-Life,
pubmed-meshheading:4723773-Hydrogen-Ion Concentration,
pubmed-meshheading:4723773-Kinetics,
pubmed-meshheading:4723773-Pentoses,
pubmed-meshheading:4723773-Plants,
pubmed-meshheading:4723773-Temperature,
pubmed-meshheading:4723773-Time Factors,
pubmed-meshheading:4723773-Tritium,
pubmed-meshheading:4723773-Uridine Diphosphate Sugars
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pubmed:year |
1973
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pubmed:articleTitle |
Synthesis, characterization and properties of uridine 5'-( -D-apio-D-furanosyl pyrophosphate).
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pubmed:publicationType |
Journal Article
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