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• W2120155276 abstract "DesII is a radical S-adenosylmethionine (SAM) enzyme that catalyzes the C4-deamination of TDP-4-amino-4,6-dideoxyglucose through a C3 radical intermediate. However, if the C4 amino group is replaced with a hydroxy group (to give TDP-quinovose), the hydroxy group at C3 is oxidized to a ketone with no C4-dehydration. It is hypothesized that hyperconjugation between the C4 CN/O bond and the partially filled p orbital at C3 of the radical intermediate modulates the degree to which elimination competes with dehydrogenation. To investigate this hypothesis, the reaction of DesII with the C4-epimer of TDP-quinovose (TDP-fucose) was examined. The reaction primarily results in the formation of TDP-6-deoxygulose and likely regeneration of TDP-fucose. The remainder of the substrate radical partitions roughly equally between C3-dehydrogenation and C4-dehydration. Thus, changing the stereochemistry at C4 permits a more balanced competition between elimination and dehydrogenation." @default.
• W2120155276 created "2016-06-24" @default.
• W2120155276 creator A5036116867 @default.
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• W2120155276 date "2014-11-21" @default.
• W2120155276 modified "2023-09-27" @default.
• W2120155276 title "Mechanistic Studies of the Radical<i>S</i>-Adenosylmethionine Enzyme DesII with TDP-<scp>D</scp>-Fucose" @default.
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• W2120155276 doi "https://doi.org/10.1002/anie.201409540" @default.
• W2120155276 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4293265" @default.
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