DIRECTED APPROACHES TO REACTIVE MAILLARD INTERMEDIATES - FORMATION OFA NOVEL MINO-2-HYDROXY-4-HYDROXYMETHYL-2-CYCLOPENTEN-1-ONE (CYPENTODINE)

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 l ow yield as a triacetylated 1,2-enol. We have prepared a 4,5-di-O-tosy l Amadori product as an activated precursor to AP-ene-dione. Incubatio n of this precursor under physiological conditions yields a novel cycl opentenone aminoreductone, ino-2-hydroxy-4-hydroxymethyl-2-cyclopenten -1-one, presumably derived from internal cyclization of AP-ene-dione. Copyright (C) 1996 Elsevier Science Ltd