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Originally published In Press as doi:10.1074/jbc.M107529200 on November 28, 2001

J. Biol. Chem., Vol. 277, Issue 7, 4867-4873, February 15, 2002
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Novel Protein Modification by Kynurenine in Human Lenses*

Santiago VazquezDagger , J. Andrew Aquilina, Joanne F. Jamie§, Margaret M. Sheil, and Roger J. W. Truscott

From the Australian Cataract Research Foundation and § Department of Chemistry, University of Wollongong, New South Wales 2522, Australia and Department of Chemistry, Macquarie University, New South Wales 2109, Australia

It is known that human lenses increase in color and fluorescence with age, but the molecular basis for this is not well understood. We demonstrate here that proteins isolated from human lenses contain significant levels of the UV filter kynurenine covalently bound to histidine and lysine residues. Identification was confirmed by synthesis of the kynurenine amino acid adducts and comparison of the chromatographic retention times and mass spectra of these authentic standards with those of corresponding adducts isolated from human lenses following acid hydrolysis. Using calf lens proteins as a model, covalent binding of kynurenine to lens proteins has been shown to proceed via side chain deamination in a manner analogous to that observed for the related UV filter, 3-hydroxykynurenine O-beta -D-glucoside. Levels of histidylkynurenine and lysylkynurenine were low in human lenses in subjects younger than 30, but thereafter increased in concentration with the age of the individual. Post-translational modification of lens proteins by tryptophan metabolites therefore appears to be responsible, at least in part, for the age-dependent increase in coloration and fluorescence of the human lens, and this process may also be important in other tissues in which up-regulation of tryptophan catabolism occurs.

* This work was supported by a grant from the National Health and Medical Research Council of Australia (NHMRC). Grants from the Australian Research Council (ARC), the Ramaciotti Foundation, and the University of Wollongong enabled the purchase of the mass and NMR spectrometers used in this work.The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

Dagger Current address: Dept. of Biological Chemistry, University of Michigan Medical Center, Ann Arbor, MI 48109-0606.

To whom correspondence should be addressed: Australian Cataract Research Foundation, Dept. of Chemistry, University of Wollongong, New South Wales 2522, Australia. Tel.: 61-2-42213503; Fax: 61-2-42214287; E-mail: roger_truscott@uow.edu.au.

Copyright © 2002 by The American Society for Biochemistry and Molecular Biology, Inc.
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