Directed approaches to reactive Maillard intermediates: Formation of a novel 3-alkylamino-2-hydroxy-4-hydroxymethyl-2-cyclopenten-1-one ('cypentodine')

Article abstract of DOI:10.1016/0040-4039(96)00959-8

Dehydration of the 4- and 5-hydroxyls of an Amadori product would lead to a reactive potential cross-linker, 1,4,5-trideoxy-1-alkylamino-2,3-hexulos-4-ene (AP-ene-dione) which has as yet only been isolated in low yield as a triacetylated 1,2-enol. We have prepared a 4,5-di-O-tosyl Amadori product as an activated precursor to AP-ene-dione. Incubation of this precursor under physiological conditions yields a novel cyclopentenone aminoreductone, 3-alkylamino-2-hydroxy-4-hydroxymethyl-2-cyclopenten-1-one, presumably derived from internal cyclization of AP-ene-dione.