Abstract
UV irradiation of 5-azido-2'-deoxyuridine in water provides up to seven products. All likely result from a pivotal azirene, formed by the intramolecular rearrangement of the initially formed nitrene, that undergoes nucleophilic addition at its C5 position. This study strongly suggests that only nucleophilic amino acid residues in close proximity are cross-linkable in photolabeling experiments by using the 5-azidouracil photophore.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Azides / chemical synthesis*
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Azides / chemistry
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Binding Sites
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Carbon / chemistry
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Chemistry, Organic / methods*
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Cross-Linking Reagents / chemistry
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DNA / chemistry
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Deoxyuracil Nucleotides / chemical synthesis*
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Deoxyuracil Nucleotides / chemistry
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Deoxyuridine / chemical synthesis*
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Deoxyuridine / chemistry*
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Drug Design
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Hydrogen-Ion Concentration
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Light
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Models, Chemical
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Molecular Structure
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Photochemistry / methods*
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Ultraviolet Rays
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Water / chemistry
Substances
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Azides
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Cross-Linking Reagents
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Deoxyuracil Nucleotides
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Water
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5-azido-2'-deoxyuridine 5'-triphosphate
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Carbon
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DNA
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Deoxyuridine