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Unexpected Carbonyl Mobility in Aminoketoses: The Key to Major Maillard Crosslinks
Author(s) -
Biemel Klaus M.,
Conrad Jürgen,
Lederer Markus O.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020301)41:5<801::aid-anie801>3.0.co;2-i
Subject(s) - maillard reaction , pentosidine , chemistry , sugar , organic chemistry , stereochemistry , biochemistry , glycation , receptor
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 N ε 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.