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The non-oxidative degradation of ascorbic acid at physiological conditions
Open accessAbstract
The degradation of L-ascorbate (AsA) and its primary oxidation products, L-dehydroascorbate (DHA) and 2,3-L-diketogulonate (2, 3-DKG) were studied under physiological conditions. Analysis determined that L-erythrulose (ERU) and oxalate were the primary degradation products of ASA regardless of which compound was used as the starting material. The identification of ERU was determined by proton decoupled (13)C-nuclear magnetic resonance spectroscopy, and was quantified by high performance liquid chromatography, and enzymatic analysis. The molar yield of ERU from 2,3-DKG at pH 7.0 37 degrees C and limiting O(2)97%. This novel ketose product of AsA degradation, was additionally qualitatively identified by gas-liquid chromatography, and by thin layer chromatography. ERU is an extremely reactive ketose, which rapidly glycates and crosslinks proteins, and therefore may mediate the AsA-dependent modification of protein (ascorbylation) seen in vitro, and also proposed to occur in vivo in human lens during diabetic and age-onset cataract formation.
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Cites
The Pecking Order of Free Radicals and Antioxidants: Lipid Peroxidation, α-Tocopherol, and Ascorbate
Buettner, G. R. (1993) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1993.1074 · Cited by 2,417
Hydrogen peroxide mediates amyloid β protein toxicity
Behl, C. (1994) · Cell · doi:10.1016/0092-8674(94)90131-7 · Cited by 2,074
Cited by
Ascorbic acid: Chemistry, biology and the treatment of cancer
Du, J., Cullen, J. J., & Buettner, G. R. (2012) · Biochimica et Biophysica Acta (BBA) - Reviews on Cancer · doi:10.1016/j.bbcan.2012.06.003 · Cited by 1,070
Interplay between the human gut microbiome and host metabolism
Visconti, A., Le Roy, C. I., Rosa, F., Rossi, N., Martin, T. C., Mohney, R. P., Li, W., de Rinaldis, E., Bell, J. T., Venter, J. C., et al. (2019) · Nature Communications · doi:10.1038/s41467-019-12476-z · Cited by 782
Vitamin C. Biosynthesis, recycling and degradation in mammals
Linster, C. L., & Van Schaftingen, E. (2007) · The FEBS Journal · doi:10.1111/j.1742-4658.2006.05607.x · Cited by 757
Ascorbic acid metabolism and functions: A comparison of plants and mammals
Smirnoff, N. (2018) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2018.03.033 · Cited by 667
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Young, J. I., Züchner, S., & Wang, G. (2015) · Annual Review of Nutrition · doi:10.1146/annurev-nutr-071714-034228 · Cited by 319
Metadata
- Authors
- Simpson, G. L. W., & Ortwerth, B. J.
- Venue
- Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease
- Publisher
- Elsevier BV
- Published
- 2000-04
- Volume
- 1501
- Issue
- 1
- Pages
- 12-24
- ISSN
- 0925-4439 (ISSN-L)
- OpenAlex
- W2079021848
- Cited by
- 158
- References
- 2
- FWCI
- 4.18
- Type
- journal article
- Language
- en
- Open access
- bronze
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- Simpson, G. L. W., & Ortwerth, B. J. (2000). The non-oxidative degradation of ascorbic acid at physiological conditions. Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease. https://doi.org/10.1016/s0925-4439(00)00009-0
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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