Document Detail

Characterization and detection of lysine-arginine cross-links derived from dehydroascorbic acid.
MedLine Citation:
PMID:  15013385     Owner:  NLM     Status:  MEDLINE    
Covalently cross-linked proteins are among the major modifications caused by the advanced Maillard reaction. So far, the chemical nature of these aggregates is largely unknown. L-dehydroascorbic acid (DHA, 5), the oxidation product of L-ascorbic acid (vitamin C), is known as a potent glycation agent. Identification is reported for the lysine-arginine cross-links N6-[2-[(4-amino-4-carboxybutyl)amino]-5-(2-hydroxyethyl)-3,5-dihydro-4H-imidazol-4-ylidene]-L-lysine (9), N6-[2-[(4-amino-4-carboxybutyl)amino]-5-(1,2-dihydroxyethyl)-3,5-dihydro-4H-imidazol-4-ylidene]-L-lysine (11), and N6-[2-[(4-amino-4-carboxybutyl)amino]-5-[(1S,2S)-1,2,3-trihydroxypropyl]-3,5-dihydro-4H-imidazol-4-ylidene]-L-lysine (13). The formation pathways could be established starting from dehydroascorbic acid (5), the degradation products 1,3,4-trihydroxybutan-2-one (7, L-erythrulose), 3,4-dihydroxy-2-oxobutanal (10, L-threosone), and L-threo-pentos-2-ulose (12, L-xylosone) were proven as precursors of the lysine-arginine cross-links 9, 11, and 13. Products 9 and 11 were synthesized starting from DHA 5, compound N6-[2-[(4-amino-4-carboxybutyl)amino]-5-[(1S,2R)-1,2,3-trihydroxypropyl]-3,5-dihydro-4H-imidazol-4-ylidene]-L-lysine (16) via the precursor D-erythro-pentos-2-ulose (15). The present study revealed that the modification of lysine and arginine side chains by DHA 5 is a complex process and could involve a number of reactive carbonyl species.
Oliver Reihl; Markus O Lederer; Wolfgang Schwack
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Carbohydrate research     Volume:  339     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2004 Feb 
Date Detail:
Created Date:  2004-03-11     Completed Date:  2004-11-04     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  483-91     Citation Subset:  IM    
Institut für Lebensmittelchemie (170), Universität Hohenheim, Garbenstr 28, D-70593 Stuttgart, Germany.
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MeSH Terms
Arginine / chemistry*
Cross-Linking Reagents / chemistry
Dehydroascorbic Acid / chemistry*
Lysine / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Tetroses / chemistry
Reg. No./Substance:
0/Cross-Linking Reagents; 0/Tetroses; 1758-51-6/erythrose; 490-83-5/Dehydroascorbic Acid; 56-87-1/Lysine; 74-79-3/Arginine

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