The glycation of proteins by glucose has been linked to the development of diabetic complications and other diseases. Early glycation is thought to involve the reaction of glucose with N-terminal and lysyl side chain amino groups to form Schiff's base and fructosamine adducts. The formation of the α-oxoaldehydes, glyoxal, methylglyoxal and 3-deoxyglucosone, in early glycation was investigated. Glucose (50 mM) degraded slowly at pH 7.4 and 37 °C to form glyoxal, methylglyoxal and 3-deoxyglucosone throughout a 3-week incubation period. Addition of t-BOC-lysine and human serum albumin increased the rate of formation of α-oxoaldehydes - except glyoxal and methylglyoxal concentrations were low with albumin, as expected from the high reactivity of glyoxal and methylglyoxal with arginine residues. The degradation of fructosyl-lysine also formed glyoxal, methylglyoxal and 3-deoxyglucosone. α-Oxoaldehyde formation was dependent on the concentration of phosphate buffer and availability of trace metal ions. This suggests that α-oxoaldehydes were formed in early glycation from the degradation of glucose and Schiff's base adduct. Since α-oxoaldehydes are important precursors of advanced glycation adducts, these adducts may be formed from early and advanced glycation processes. Short periods of hyperglycaemia, as occur in impaired glucose tolerance, may be sufficient to increase the concentrations of α-oxoaldehydes in vivo.
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Research Article|
November 08 1999
Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose
Paul J. THORNALLEY;
Paul J. THORNALLEY
1Department of Biological Sciences, University of Essex, Central Campus, Wivenhoe Park, Colchester CO4 3SQ, Essex, U.K.
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Annika LANGBORG;
Annika LANGBORG
1Department of Biological Sciences, University of Essex, Central Campus, Wivenhoe Park, Colchester CO4 3SQ, Essex, U.K.
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Harjit S. MINHAS
Harjit S. MINHAS
1
1Department of Biological Sciences, University of Essex, Central Campus, Wivenhoe Park, Colchester CO4 3SQ, Essex, U.K.
1To whom correspondence should be addressed (e-mail thorp@essex.ac.uk).
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Publisher: Portland Press Ltd
Received:
June 07 1999
Revision Received:
July 30 1999
Accepted:
August 31 1999
Online ISSN: 1470-8728
Print ISSN: 0264-6021
The Biochemical Society, London © 1999
1999
Biochem J (1999) 344 (1): 109–116.
Article history
Received:
June 07 1999
Revision Received:
July 30 1999
Accepted:
August 31 1999
Citation
Paul J. THORNALLEY, Annika LANGBORG, Harjit S. MINHAS; Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. Biochem J 15 November 1999; 344 (1): 109–116. doi: https://doi.org/10.1042/bj3440109
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