Radical reactions of carbohydrates. Part 3. An electron spin resonance investigation of base-catalysed rearrangements of radicals derived from D-glucose and related compounds
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 2,p. 169-179
- https://doi.org/10.1039/p29820000169
Abstract
E.s.r. observations have been made on the rearrangements of radicals formed from the reaction between ·OH and a series of simple sugars at pH > 7. Two types of semidione have been identified [for example D-glucose gives geometric isomers of both HOCH2·CHOH·CHOH·CHOH·C(O·)C(O–)H and HOCH2·C(O·)C(O–)H]: their formation provides two routes to radical-induced base-catalysed degradation of carbohydrates, involving ring opening at the O–C(1) bond and, in the second case. C–C cleavage. We suggest that the latter reaction involves a Grob-type fragmentation and that this may account for the formation of malondialdehyde in these systems.Keywords
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