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C-1 Oxidation/C-2 Reduction Isomerization of Unprotected Aldoses Induced by Light/Ketone.

Unprotected aldoses in water undergo an isomerization reaction via a radical pathway when irradiated with light in the presence of water-soluble benzophenone.  Whereas its anomeric carbon (C-1) is oxidized to a carboxy group, the hydroxy group on the C-2 carbon is replaced by hydrogen.  The generated 2-deoxy lactones are readily reduced to the corresponding 2-deoxy aldoses, which are often contained in bioactive compounds.