Radical reactions of carbohydrates. Part 4. Electron spin resonance studies of radical-induced oxidation of some aldopentoses, sucrose, and compounds containing furanose rings
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 675-683
- https://doi.org/10.1039/p29830000675
Abstract
E.s.r. spectra detected when ·OH reacts with the aldopentoses xylose and ribose are attributed to pyranose ring radicals, formed in essentially unselective attack; in contrast, in the corresponding reactions of the model compound tetrahydrofurfuryl alcohol, as well as some isopropylidene derivatives of glucofuranose, the hydrogen atoms on the carbon atoms adjacent to oxygen in a furanose ring are activated towards abstraction. A similar activation, evidently stereoelectronic in origin, is also proposed to account for the enhanced reactivity of C(5′)–H in the furanose ring of sucrose, a finding which may have particular relevance to the mechanism of radiation damage in DNA.Keywords
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