Unexpected Carbonyl Mobility in Aminoketoses: The Key to Major Maillard Crosslinks

The novel dideoxyosones 1 and 2 were shown to be precursors of the important in vivo crosslinks glucosepane and pentosidine. In 1 and 2, the lysine Nε atom is directly bonded to C1 of the original sugar group. The formation of these compounds proceeds through carbonyl shifts along the entire carbohy...

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Veröffentlicht in:	Angewandte Chemie International Edition 2002-03, Vol.41 (5), p.801-804
Hauptverfasser:	Biemel, Klaus M., Conrad, Jürgen, Lederer, Markus O.
Format:	Artikel
Sprache:	eng
Schlagworte:	Aging - physiology Amino Sugars - chemistry Arginine - chemistry carbohydrates Carbon Radioisotopes Diabetes Mellitus - physiopathology Glycation End Products, Advanced - chemistry heterocycles Humans Lysine - chemistry Maillard reaction protein cross-linking Radioactive Tracers structure elucidation
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Beschreibung
Zusammenfassung:	The novel dideoxyosones 1 and 2 were shown to be precursors of the important in vivo crosslinks glucosepane and pentosidine. In 1 and 2, the lysine Nε atom is directly bonded to C1 of the original sugar group. The formation of these compounds proceeds through carbonyl shifts along the entire carbohydrate backbone.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/1521-3773(20020301)41:5<801::AID-ANIE801>3.0.CO;2-I