Influence of glutathione fructosylation on its properties.
Incubation of fructose and glutathione leads to the formation of N-2-deoxy-glucos-2-yl glutathione as the major glycation product, with characteristic positive ion at 470 Th in LC-MS spectra. Glutathione disulfide and fructose generate two compounds: N-2-deoxy-glucos-2-yl glutathione disulfide (m/z=775 Th) and bis di-N,N'-2-deoxy-glucos-2-yl glutathione disulfide (m/z=937 Th). N-2-deoxy-glucos-2-yl glutathione is 2.5-fold less effective than glutathione in reducing dehydroascorbic acid. Glutathione peroxidase and glutahione-S-transferase exhibit marginal activity toward N-2-deoxy-glucos-2-yl glutathione, while glyoxalase I shows 44.9% of the enzyme's specific activity. Glutathione reductase demonstrates 6.9% of the enzyme's specific activity with bis di-N,N'-2-deoxy-glucos-2-yl glutathione, while with mono-N-glucosyl glutathione disulfide retained 5 6.1% of the original activity. Glutathione reductase could not reduce N-2-deoxy-glucos-2-yl glutathione in mixed disulfide with gammaS-crystallin, but reduced glutathione in mixed disulfide with gammaS-crystallin by 90%. The presence of N-2-deoxy-glucos-2-yl glutathione in mixed disulfide with gammaS-crystallin makes this molecule more susceptible to unfolding than native gammaS-crystallin.
Linetsky
Mikhail
M
Mason Eye Institute, University of Missouri, Columbia, MO 65201, USA. LinetskyM@health.missouri.edu
Shipova
Ekaterina V
EV
Argirov
Ognyan K
OK
D005632:Fructose / Q000032:analysis / Q000737:chemistry*; D005978:Glutathione / Q000032:analysis / Q000737:chemistry*; D013329:Structure-Activity Relationship
D005632:Fructose; D005978:Glutathione