New Melanoidin-like Maillard Polymers from 2-Deoxypentoses

In the 2-deoxy-d-ribose/methyl 4-aminobutyrate Maillard system a trapped N-substituted 2-(hydroxymethyl)pyrrole is one of the major products. However, nontrapped representatives of this type of compound were hitherto not found in other Maillard model systems, indicating their extraordinary reactivit...

Full description

Saved in:
Bibliographic Details
Published in:Journal of agricultural and food chemistry 1998-01, Vol.46 (1), p.104-110
Main Authors: Tressl, Roland, Wondrak, Georg T., Krüger, Ralph-Peter, Rewicki, Dieter
Format: Article
Language:English
Subjects:
2-DEOXY-D-RIBOSE/METHYLAMINE MAILLARD MODEL SYSTEM
AMINAS
AMINE
AMINES
ANTIOXIDANTES
ANTIOXIDANTS
ANTIOXYDANT
Applied sciences
Exact sciences and technology
MAILLARD REACTION
MELANODINS
METHYLAMINE
MODELE
MODELOS
MOLECULAR WEIGHT
MONOSACARIDOS
MONOSACCHARIDE
MONOSACCHARIDES
Organic polymers
PESO MOLECULAR
Physicochemistry of polymers
POIDS MOLECULAIRE
POLIMEROS
POLYMERE
Polymerization
POLYMERS
Preparation, kinetics, thermodynamics, mechanism and catalysts
PYRROLES
REACCION DE MAILLARD
REACTION DE MAILLARD
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:In the 2-deoxy-d-ribose/methyl 4-aminobutyrate Maillard system a trapped N-substituted 2-(hydroxymethyl)pyrrole is one of the major products. However, nontrapped representatives of this type of compound were hitherto not found in other Maillard model systems, indicating their extraordinary reactivity. Model experiments with 2-deoxy-d-ribose/methylamine enabled the detection of N-methyl-2-(hydroxymethyl)pyrrole (1) and some derived linear oligomers (2, 3) as minor components. Consequently, 1 was synthesized and its oligomerization studied under very mild acidic conditions. The deformylated dimeric bis(N-methyl-2-pyrrolyl)methane (2) and trimeric N-methyl-2,5-bis(N-methyl-2-pyrrolylmethyl)pyrrole (3) were characterized by GC/MS and NMR. Higher regular oligomers up to 6 N-methyl-2-pyrrolylmethyl units as well as corresponding dehydro-oligomers up to 12 units were identified by MALDI-TOF-MS. A complementary experiment starting with N-methyl-2-hydroxy[13C]methylpyrrole ([13CH2OH]-1) confirmed the structure and the oligomerization pathway. The possible significance of this type of model oligomer for the melanoidin formation in Maillard reactions is discussed. The antioxidative activity of the isolated dimer and trimer was tested in Fe(III)−thiocyanate and DPPH assays. Keywords: Maillard system 2-deoxy-d-ribose/methylamine; oligomerization of N-methyl-2-hydroxymethyl(and hydroxy[13C]methyl)pyrrole; antioxidative activity; model compounds for melanoidins
ISSN:0021-8561
1520-5118
DOI:10.1021/jf970657c