New Melanoidin-like Maillard Polymers from 2-Deoxypentoses.

摘要: In the 2-deoxy-d-ribose/methyl 4-aminobutyrate Maillard system a trapped N-substituted 2-(hydroxymethyl)pyrrole is one of major products. However, nontrapped representatives this type compound were hitherto not found in other model systems, indicating their extraordinary reactivity. Model experiments with 2-deoxy-d-ribose/methylamine enabled detection N-methyl-2-(hydroxymethyl)pyrrole (1) and some derived linear oligomers (2, 3) as minor components. Consequently, 1 was synthesized its oligomerization studied under very mild acidic conditions. The deformylated dimeric bis(N-methyl-2-pyrrolyl)methane (2) trimeric N-methyl-2,5-bis(N-methyl-2-pyrrolylmethyl)pyrrole (3) characterized by GC/MS NMR. Higher regular up to 6 N-methyl-2-pyrrolylmethyl units well corresponding dehydro-oligomers 12 identified MALDI-TOF-MS. A complementary experiment starting N-methyl-2-hydroxy[13C]methylpyrrole ([13CH2OH]-1) confirmed structure and...