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Triosidines: novel Maillard reaction products and cross-links from the reaction of triose sugars with lysine and arginine residues

Tessier, Frederic J. and Monnier, Vincent M. and Sayre, Lawrence M. and Kornfield, Julia A. (2003) Triosidines: novel Maillard reaction products and cross-links from the reaction of triose sugars with lysine and arginine residues. Biochemical Journal, 369 (3). pp. 705-719. ISSN 0264-6021. PMCID PMC1223106.

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The role of the highly reactive triose sugars glyceraldehyde and glyceraldehyde-3-phosphate in protein cross-linking and other amino acid modifications during the Maillard reaction was investigated. From the incubation of glyceraldehyde with Nα-acetyl-l-lysine and Nα-acetyl-l-arginine, we isolated four new Maillard reaction pyridinium compounds named ‘triosidines'. Two of them, ‘lys-hydroxy-triosidine’ {1-(5-amino-5-carboxypentyl)-3-[(5-amino-5-carboxypentylamino)methyl]-5-hydroxypyridinium} and ‘arg-hydroxy-triosidine’ {2-(4-amino-4-carboxybutylamino)-8-(5-amino-5-carboxypentyl)-6-hydroxy-3,4-dihydro-pyrido[2,3-d]pyrimidin-8-ium} are fluorescent, UV-active Lys—Lys and Lys—Arg cross-links respectively. Their structures were identified by NMR and MS. In addition, two UV-active lysine adducts, ‘trihydroxy-triosidine’ [1-(5-amino-5-carboxypentyl)-3,4-dihydroxy-5-(hydroxymethyl)pyridinium] and ‘triosidine carbaldehyde’ [1-(5-amino-5-carboxypentyl)-3-formylpyridinium] were tentatively identified by MS. All structures involve six sugar-derived carbons as part of the heterocyclic ring. Of the two novel cross-links, only arg-hydroxy-triosidine was formed by glyceraldehyde-3-phosphate, an intermediate metabolite of the glycolytic pathway. Lys-hydroxy-triosidine and arg-hydroxy-triosidine were detected in human and porcine corneas treated with glyceraldehyde. The HPLC-fluorescence identification was confirmed by MS. Triosidines were also formed from dihydroxyacetone, a widely used artificial sun-tanning agent. Triosidines are expected to be useful tools in tissue engineering, where the utilization of highly reactive sugars is needed to stabilize the loose matrix. In addition, they are expected to be present in selected biological conditions, such as on consumption of a high fructose diet, and syndromes associated with high glyceraldehyde excretion, such as Fanconi Syndrome, fructose-1,6-diphosphatase deficiency and tyrosinaemia.

Item Type:Article
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URLURL TypeDescription CentralArticle
Kornfield, Julia A.0000-0001-6746-8634
Additional Information:© 2003 Biochemical Society. Received 26 April 2002/23 September 2002 ; accepted 14 October 2002. Published as BJ Immediate Publication 14 October 2002. We thank Dr Marcus Glomb for his gift of argpyrimidine standard and Dr Robert Salomon (Department of Chemistry, Case Western Reserve University, OH, U.S.A.) for assistance with computerized systematic nomenclature. We also thank Drs David Sell and Tiberiu G. Mustata (Institute of Pathology, Case Western Reserve University, OH, U.S.A.) for help with determination of glyceraldehyde contaminants in commercial batches. This work was supported by a grant from the National Institute of Aging (AG 18629) and in part by the National Eye Institute (EY07099).
Funding AgencyGrant Number
NIHAG 18629
National Institute of AgingUNSPECIFIED
National Eye InstituteUNSPECIFIED
Subject Keywords:dihydroxyacetone, glycation, glyceraldehyde, glyceraldehyde-3-phosphate, tissue engineering
Issue or Number:3
PubMed Central ID:PMC1223106
Record Number:CaltechAUTHORS:20200716-141801845
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Official Citation:Frederic J. TESSIER, Vincent M. MONNIER, Lawrence M. SAYRE, Julia A. KORNFIELD; Triosidines: novel Maillard reaction products and cross-links from the reaction of triose sugars with lysine and arginine residues. Biochem J 1 February 2003; 369 (3): 705–719. doi:
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:104412
Deposited By: Tony Diaz
Deposited On:16 Jul 2020 21:28
Last Modified:16 Jul 2020 21:28

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