Trapping a Labile Adduct Formed between an ortho-Quinone Methide and 2′-Deoxycytidine
| Autor: | Yiu-Fai Lam, Steven E. Rokita, Michael P. McCrane, Ying Lin, Emily E. Weinert, Peter F. Scholl, Eugene P. Mazzola |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
chemistry.chemical_classification
Quenching (fluorescence) Alkylation Molecular Structure Organic Chemistry Substituent Stereoisomerism Aromaticity Photochemistry Deoxycytidine Biochemistry Quinone methide Adduct chemistry.chemical_compound chemistry Indolequinones Physical and Theoretical Chemistry Oxidation-Reduction Derivative (chemistry) Alkyl |
| Zdroj: | Organic Letters. 13:1186-1189 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol200071p |
| Popis: | Selective oxidation by bis[(trifluoroacetoxy)iodo]benzene (BTI) provides an effective trap for quenching adducts formed reversibly between dC and an ortho-quinone methide (QM) under physiological conditions. A model adduct generated by 4-methyl-o-QM and 2'-deoxycytidine is rapidly converted by intramolecular cyclization and loss of aromaticity to a characteristic product for quantifying QM alkylation. However, BTI induces a surprising rearrangement driven by overoxidation of a derivative lacking an alkyl substituent at the 4-position of the QM. |
| Databáze: | OpenAIRE |
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