Identification of 3,4-dihydroxy-2-oxo-butanal (L-threosone) as an intermediate compound in oxidative degradation of dehydro-L-ascorbic acid and 2,3-diketo-L-gulonic acid in a deuterium oxide phosphate buffer

Bioscience, Biotechnology and Biochemistry

Volumn 65, Issue 8, 2001, Pages 1707-1712

  Nishikawa, Yoko ^a   Toyoshima, Yuka ^a   Kurata, Tadao ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

Degradation; Diketo L gulonic acid; L ascorbic acid; L threosone

Indexed keywords

2,3 DIOXOGULONIC ACID; 3,4 DIHYDROXY 2 OXO BUTANAL; 3,4-DIHYDROXY-2-OXO-BUTANAL; ALDEHYDE; BUFFER; DEHYDROASCORBIC ACID; DEUTERIUM OXIDE; HYDRAZONE DERIVATIVE; OXALIC ACID; PHOSPHATE;

ARTICLE; CHEMISTRY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; ULTRAVIOLET SPECTROPHOTOMETRY;

2,3-DIKETOGULONIC ACID; ALDEHYDES; BUFFERS; CHROMATOGRAPHY, LIQUID; DEHYDROASCORBIC ACID; DEUTERIUM OXIDE; HYDRAZONES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR WEIGHT; OXALIC ACID; OXIDATION-REDUCTION; PHOSPHATES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0035431221     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.1707     Document Type: Article

References (23)

1. Yamazaki, I. and Piette, L. H., Mechanism of free radical formation and disappearance during the ascorbic acid oxidase and peroxidase reactions. Biochim. Biophys. Acta, 50, 62-69 (1961).
2. Weis, W., Zubrzycki, Z., and Staudinger, H., Redox behavior of L(+)-semidehydro-ascorbic acid. Hoppe Seyler's Z. Physiol. Chem., 349, 279-282 (1968).
3. Wells, W. W., Xu, D. P., Yang, Y., and Rocque, P.A., Mammalian thioltransferase (glutaredoxin) and protein disulfide isomerase. J. Biol. Chem., 265, 15361-15364 (1990).
4. Borsook, H., Davenport, H. W., Jeffreys, C. E. P., and Warner, R. C., The oxidation of ascorbic acid and its reduction in vitro and in vivo. J. Biol. Chem., 117, 237-279 (1937).
5. Kagawa, Y., Enzymatic studies on ascorbic acid catabolism in animals: I. Catabolism of 2,3-diketo-L-gulonic acid. J. Biochem., 51, 134-144 (1962).
6. Nishikawa, Y. and Kurata, T., Chemical characteristics of dehydro-L-ascorbic acid. Biosci. Biotechnol. Biochem., 64, 1651-1655 (2000).
7. Bode, A. M., Cunningham, L., and Rose, R. C., Spontaneous decay of oxidized ascorbic acid (dehydro-L-ascorbic acid) evaluated by high-pressure liquid chromatography. Clin. Chem., 36, 1807-1809 (1990).
8. Nagaraj, R. H. and Monnier, V. M., Protein modification by the degradation products of ascorbate: formation of a novel pyrrole from the Maillard reaction of L-threose with proteins. Biochim. Biophys. Acta, 1253, 75-84 (1995).
9. Nishikawa, Y. and Kurata, T., Structure and chemical characteristics of dehydro-L-ascorbic acid in solutions. Food Sci. Technol. Int. Tokyo, 4, 155-158 (1998).
10. Nishikawa, Y. and Kurata, T., Interconversion between dehydro-L-ascorbic acid and L-ascorbic acid. Biosci. Biotechnol. Biochem., 64, 476-483 (2000).
11. Otsuka, M., Kurata, T., and Arakawa, N., Isolation and characterization of an intermediate product in the degradation of 2,3-diketo-L-gulonic acid. Agric. Biol. Chem., 50, 531-533 (1986).
12. Kimoto, E., Tanaka, H., Ohmori, T., and Choami, M., Analysis of the transformation products of dehydro-L-ascorbic acid by ion-pairing high-performance liquid chromatography. Anal. Biochem., 214, 38-44 (1993).
13. Jung, C. and Wells, W. W., Spontaneous conversion of L-dehydroascorbic acid to L-ascorbic acid and L-erythroascorbic acid. Arch. Biochem. Biophys., 355, 9-14 (1998).
14. Kurata, T. and Fujimaki, M., Formation of 3-keto-4-deoxypentosone and 3-hydroxy-2-pyrone by the degradation of dehydro-L-ascorbic acid. Agr. Biol. Chem., 40, 1287-1291 (1976).
15. Simpson, G. and Ortwerth, B. J., The non-oxidative degradation of ascorbic acid at physiological conditions. Biochim. Biophys. Acta, 1501, 12-24 (2000).
16. Ortwerth, B. J., Slight, S. H., Prabhakaram, M., Sun, Y., and Smith, J. B., Site-specific glycation of lens crystallins by ascorbic acid. Biochem. Biophys. Acta, 1117, 207-215 (1992).
17. Kornig, R. J., Blobstein, S. H., and Cerami, A., Structure of carbohydrate of hemoglobin AIC. J. Biol. Chem., 253, 2992-2997 (1977).
18. Grandhee, S. K. and Monnier, V. M., Mechanism of formation of the Maillard protein cross-link. J. Biol. Chem., 266, 11649-11653 (1991).
19. Nwaka, S., Kopp, M., and Holzer, H., Expression and function of the trehalase genes NHT1 and YBR0106 in saccharomyces cerevisiae. J. Biol. Chem., 2-70, 10193-10198 (1995).
20. Ohmori, M. and Takagi, M., A facile preparation of dehydro-L-ascorbic acid-methanol solution and its stability. Agric. Biol. Chem., 42, 173-174 (1978).
21. Kushner, D. J., Baker, A., and Dunstall, T. G., Pharmacological uses and perspectives of heavy water and deuterated compounds. Can. J. Physiol. Pharmacol., 77, 79-88 (1999).
22. Rangappa, K. S., Raghavendra, M. P., Mahadevappa, D. S., and Gowda, D. C., Kinetics and mechanism of oxidation of erythro-series pentoses and hexoses by N-chloro-p-toluenesulfonamide. Carbohydrate Research, 306, 57-67 (1998).
23. Retsky, K., Freeman, M., and Frei, B., Ascorbic acid oxidation product(s) protect human low density lipoprotein against atherogenic modification. J. Biol. Chem., 268, 1304-1309 (1993).