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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
11
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pubmed:dateCreated |
2007-5-23
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pubmed:abstractText |
Novel bitriazolyl nucleosides were synthesized via the Huisgen reaction, starting with 3-azidotriazole nucleoside (1). Surprisingly, its isomer, 5-azidotriazole nucleoside (1') did not yield the corresponding Huisgen reaction products efficiently because it was rapidly reduced to amine in the presence of Cu(II)-ascorbate. The significant differences between the reactivity of these two isomers in Cu(II)-ascorbate mediated reactions are mainly due to differences in their electronic properties and steric congestion as a result of different relative positions of the azido and the ribosyl moieties.
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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 |
1477-0520
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
7
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pubmed:volume |
5
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1695-701
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pubmed:meshHeading |
pubmed-meshheading:17520136-Ascorbic Acid,
pubmed-meshheading:17520136-Azides,
pubmed-meshheading:17520136-Catalysis,
pubmed-meshheading:17520136-Copper,
pubmed-meshheading:17520136-Isomerism,
pubmed-meshheading:17520136-Microbial Sensitivity Tests,
pubmed-meshheading:17520136-Models, Chemical,
pubmed-meshheading:17520136-Nucleosides,
pubmed-meshheading:17520136-Oxidation-Reduction,
pubmed-meshheading:17520136-Triazoles
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pubmed:year |
2007
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pubmed:articleTitle |
Synthesis of bitriazolyl nucleosides and unexpectedly different reactivity of azidotriazole nucleoside isomers in the Huisgen reaction.
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pubmed:affiliation |
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. China.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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