Formation of n-(1-oxo-2,4,5,6-hydroxyhexyl)-2′-deoxyguanosine by the reaction of 2′-deoxyguanosine with 3-deoxyglucosone

Bioscience, Biotechnology and Biochemistry

Volumn 62, Issue 8, 1998, Pages 1630-1632

  Hayase, Fumitaka ^a   Kaneko, Koji ^a  

^a MEIJI UNIVERSITY   (Japan)

Author keywords

2 deoxyguanosine; 3 deoxyglucosone; Maillard reaction; Methylglyoxal; Nucleosides

Indexed keywords

EID: 0347480077     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.62.1630     Document Type: Article

References (18)

1. Shin, D. B., Hayase, F., and Kato, H., Polymerization of proteins caused by the reaction with sugars and the formation of 3-deoxyglucosone under physiological conditions. Agric. Biol. Chem., 52, 1451-1458 (1998).
2. Hayase, F., Liang, Z. Q., Suzuki, Y., Chuyen, N. V., Shinoda, T., and Kato, H., Enzymatic metabolism of 3-deoxyglucosone, a Maillard intermediate. Amino Acid, 1, 307-318 (1991).
3. Knecht, K. J., Feather, M. S., and Baynes, J. W., Detection of 3-deoxyglucosone in human urine and plasma: Evidence for intermediate stages of the Maillard reaction in vivo. Arch. Biochem. Biophys., 294, 130-137 (1992).
4. Niwa, T., Takeda, N., Yoshizumi, H., Tatematsu, A., Ohara, M., Tomiyama, S., and Niimura, K., Presence of 3-deoxyglucosone, A potent protein crosslinking intermediate of Maillard reaction, in diabetic serum. Biochem. Biophys. Res. Commun., 196, 837-843 (1993).
5. Yamada, H., Miyata, S., Igaki, N., Yatabe, H., Miyauchi, Y., Ohara, T., Sakai, M., Shoda, H., Oimomi, M., and Kasuga, M., Increase in 3-deoxyglucosone levels in diabetic rat plasma. J. Biol. Chem., 269, 20275-20280 (1994).
6. Lai, S., Kappler, F., Walker, M., Orchard, T. J., Beisswenger, P. J., Szwergold, B. S., and Brown, T. R., Quantitation of 3-deoxyglucosone levels in human plasma. Arch. Biochem. Biophys., 342, 254-260 (1997).
7. Szwergold, B. S., Kappler, F., and Brown, T. R., Identification of fructose 3-phosphate in the lens of diabetic rats. Science, 247, 451-454 (1990).
8. Hayase, F. and Kato, H., Maillard reaction products: Safety and physiologic effects. Comm. Agric. Food Chem., 3, 111-128 (1994).
9. Cho, R. K., Okitani, A., and Kato, H., Polymerization of proteins and impairment of their arginine residues due to intermediate compounds in the Maillard reaction. Dev. Food Sci., 13, 439-448 (1986).
10. Kato, H., Shin, D. B., and Hayase, F., 3-Deoxyglucosone crosslinks proteins under physiological conditions. Agric. Biol. Chem., 51, 2009-2011 (1987).
11. Kato, H., Cho, R. K., Okitani, A., and Hayase, F., Responsibility of 3-deoxyglucosone for the glucose-induced polymerization of proteins. Agric. Biol. Chem., 51, 683-689 (1987).
12. Saito, G., Okitani, A., Hayase, F., and Kato, H., Characterization of tryptophan derivatives from the reaction of N“-acetyltryp-tophan with carbonyl compounds. Agric. Biol. Chem., 50, 2315-2323 (1986).
13. Hayase, F., Hinuma, H., Asano, M., Kato, H., and Arai, S., Identification of novel fluorescent pyrrolopyridinium compound formed from Maillard reaction of 3-deoxyglucosone and butyla-mine. Biosci. Biotech. Biochem., 58, 1936-1937 (1994).
14. Shinoda, T., Hayase, F., and Kato, H., Suppression of cell-cycle progression during the S phase of rat fibroblasts by 3-deoxyglucosone, a Maillard reaction intermediate. Biosci. Biotech. Biochem., 58, 2215-2219 (1994).
15. Egyiid, L. G. and Szend-Gyorgyi, A., On the regulation of cell division. Proc. Natl. Acad. Sci. U.S.A., 56, 203-207 (1966).
16. Szent-Gyorgyi, A., Egyiid, L. G., and McLaughlin, J. A., Keto-aldehydes and cell division. Science, 155, 539-541 (1967).
17. 2-(l-carboxyethyl)-guanine (CEG) as a guanine advanced glycosyla-tion end product. Biochemistry, 34, 648-655 (1995).
18. Kato, H., Chuyen, N. V., Shinoda, T., Sekiya, F., and Hayase, F., Metabolism of 3-deoxyglucosone, an intermediate compound in the Maillard reaction, administered orally or intravenously to rats. Biochim. Biophys. Acta, 1035, 71-76 (1990).