Identification of the new UV filter compound cysteine-l-3-hydroxykynurenine O-β-d-glucoside in human lenses

Peter G. Hains, Jasminka Mizdrak, Isla M. Streete, Joanne F. Jamie, Roger J W Truscott

Research output: Contribution to journalArticleResearchpeer-review

Abstract

UV filters protect the human lens and retina from UV light-induced damage. Here, we report the identification of a new UV filter, cysteine-l-3-hydroxykynurenine O-β-d-glucoside, which is present in older normal human lenses. Its structure was confirmed by independent synthesis. It is likely this novel UV filter is formed in the lens by nucleophilic attack of cysteine on the unsaturated ketone derived from deamination of 3-hydroxykynurenine O-β-d-glucoside. Quantitation studies revealed considerable variation in normal lens levels that may be traced to the marked instability of the cysteine adduct. The novel UV filter was not detected in advanced nuclear cataract lenses. Crown

LanguageEnglish
Pages5071-5076
Number of pages6
JournalFEBS Letters
Volume580
Issue number21
DOIs
Publication statusPublished - 18 Sep 2006

Fingerprint

Glucosides
Lenses
Cysteine
Deamination
Ultraviolet Rays
Ketones
Crowns
Ultraviolet radiation
Cataract
Retina
3-hydroxykynurenine

Cite this

Hains, Peter G. ; Mizdrak, Jasminka ; Streete, Isla M. ; Jamie, Joanne F. ; Truscott, Roger J W. / Identification of the new UV filter compound cysteine-l-3-hydroxykynurenine O-β-d-glucoside in human lenses. In: FEBS Letters. 2006 ; Vol. 580, No. 21. pp. 5071-5076.
@article{414e3408dc0f4ccfb9088ffae4581817,
title = "Identification of the new UV filter compound cysteine-l-3-hydroxykynurenine O-β-d-glucoside in human lenses",
abstract = "UV filters protect the human lens and retina from UV light-induced damage. Here, we report the identification of a new UV filter, cysteine-l-3-hydroxykynurenine O-β-d-glucoside, which is present in older normal human lenses. Its structure was confirmed by independent synthesis. It is likely this novel UV filter is formed in the lens by nucleophilic attack of cysteine on the unsaturated ketone derived from deamination of 3-hydroxykynurenine O-β-d-glucoside. Quantitation studies revealed considerable variation in normal lens levels that may be traced to the marked instability of the cysteine adduct. The novel UV filter was not detected in advanced nuclear cataract lenses. Crown",
author = "Hains, {Peter G.} and Jasminka Mizdrak and Streete, {Isla M.} and Jamie, {Joanne F.} and Truscott, {Roger J W}",
year = "2006",
month = "9",
day = "18",
doi = "10.1016/j.febslet.2006.08.026",
language = "English",
volume = "580",
pages = "5071--5076",
journal = "FEBS Letters",
issn = "1873-3468",
publisher = "Elsevier",
number = "21",

}

Identification of the new UV filter compound cysteine-l-3-hydroxykynurenine O-β-d-glucoside in human lenses. / Hains, Peter G.; Mizdrak, Jasminka; Streete, Isla M.; Jamie, Joanne F.; Truscott, Roger J W.

In: FEBS Letters, Vol. 580, No. 21, 18.09.2006, p. 5071-5076.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Identification of the new UV filter compound cysteine-l-3-hydroxykynurenine O-β-d-glucoside in human lenses

AU - Hains, Peter G.

AU - Mizdrak, Jasminka

AU - Streete, Isla M.

AU - Jamie, Joanne F.

AU - Truscott, Roger J W

PY - 2006/9/18

Y1 - 2006/9/18

N2 - UV filters protect the human lens and retina from UV light-induced damage. Here, we report the identification of a new UV filter, cysteine-l-3-hydroxykynurenine O-β-d-glucoside, which is present in older normal human lenses. Its structure was confirmed by independent synthesis. It is likely this novel UV filter is formed in the lens by nucleophilic attack of cysteine on the unsaturated ketone derived from deamination of 3-hydroxykynurenine O-β-d-glucoside. Quantitation studies revealed considerable variation in normal lens levels that may be traced to the marked instability of the cysteine adduct. The novel UV filter was not detected in advanced nuclear cataract lenses. Crown

AB - UV filters protect the human lens and retina from UV light-induced damage. Here, we report the identification of a new UV filter, cysteine-l-3-hydroxykynurenine O-β-d-glucoside, which is present in older normal human lenses. Its structure was confirmed by independent synthesis. It is likely this novel UV filter is formed in the lens by nucleophilic attack of cysteine on the unsaturated ketone derived from deamination of 3-hydroxykynurenine O-β-d-glucoside. Quantitation studies revealed considerable variation in normal lens levels that may be traced to the marked instability of the cysteine adduct. The novel UV filter was not detected in advanced nuclear cataract lenses. Crown

UR - http://www.scopus.com/inward/record.url?scp=33748302770&partnerID=8YFLogxK

U2 - 10.1016/j.febslet.2006.08.026

DO - 10.1016/j.febslet.2006.08.026

M3 - Article

VL - 580

SP - 5071

EP - 5076

JO - FEBS Letters

T2 - FEBS Letters

JF - FEBS Letters

SN - 1873-3468

IS - 21

ER -