Abstract
4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses.
| Language | English |
|---|---|
| Pages | 4990-4999 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 63 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 4 Jun 2007 |
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Novel human lens metabolites from normal and cataractous human lenses. / Mizdrak, Jasminka; Hains, Peter G.; Kalinowski, Danuta; Truscott, Roger J W; Davies, Michael J.; Jamie, Joanne F.
In: Tetrahedron, Vol. 63, No. 23, 04.06.2007, p. 4990-4999.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Novel human lens metabolites from normal and cataractous human lenses
AU - Mizdrak, Jasminka
AU - Hains, Peter G.
AU - Kalinowski, Danuta
AU - Truscott, Roger J W
AU - Davies, Michael J.
AU - Jamie, Joanne F.
PY - 2007/6/4
Y1 - 2007/6/4
N2 - 4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses.
AB - 4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses.
UR - http://www.scopus.com/inward/record.url?scp=34247592951&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.03.133
DO - 10.1016/j.tet.2007.03.133
M3 - Article
VL - 63
SP - 4990
EP - 4999
JO - Tetrahedron
T2 - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 23
ER -