6-Bromo-6-deoxy-l-ascorbic Acid
Open accessAbstract
Vitamin C intracellular accumulation is mediated by Na(+)-dependent vitamin C transporters SVCT1 and -2 and dehydroascorbic acid transporters GLUT1 and -3. It is unclear which pathways dominate in vivo. As a new step to resolve this issue, we identified and tested 6-bromo-6-deoxy-L-ascorbic acid as a specific candidate for SVCTs. In high performance liquid chromatography and electron paramagnetic resonance analyses, the reduced compounds ascorbic acid and 6-bromo-6-deoxy-L-ascorbic acid were similar. The oxidized products 6-bromo-6-deoxy dehydroascorbic acid (BrDHA) and dehydroascorbic acid (DHA) had comparable stabilities, based on reduction recoveries. Upon expression of GLUT1 or GLUT3 in Xenopus oocytes, BrDHA was neither transported nor bound, in contrast to robust transport of DHA. The findings were not explained by differences in the oocyte reduction of DHA and BrDHA because lysed oocytes reduced both compounds equally. Further, there was no transport of the reduced compound, 6-bromo-6-deoxy-L-ascorbic acid, by GLUT1 or GLUT3. As a prerequisite for investigating 6-bromo-6-deoxy-L-ascorbic acid transported by SVCTs, SVCT2 transport activity in oocytes was enhanced 14-fold by construction and use of a vector that added a fixed poly(A) tail to the 3' end of cRNA. For SVCT1 and SVCT2 expressed in oocytes, similar K(m) and V(max) values were observed for ascorbic acid and 6-bromo-6-deoxy-L-ascorbic acid. In human fibroblasts, predicted to have SVCT-mediated ascorbate accumulation, K(m) and V(max) values were again comparable for ascorbic acid and 6-bromo-6-deoxy-L-ascorbic acid. Using activated human neutrophils, predicted to have ascorbate accumulation mediated predominantly by DHA and GLUT transporters, 6-bromo-6-deoxy-L-ascorbic acid accumulation was <1% of accumulation when compared with ascorbic acid. We conclude that 6-bromo-6-deoxy-L-ascorbic acid is the first transport substrate identified as completely specific for SVCTs, but not GLUTs, and provide a new strategy to determine the contribution of each pathway to ascorbate accumulation.
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Dehydroascorbic acid forms a bicyclic hemiketal that resembles glucose and has high affinity for glucose transporters GLUT1 and GLUT3 (GLUT4 can be involved, but GLUT2 and GLUT5 are not).
“Dehydroascorbic acid does not resemble glucose, but it forms bicyclic hemiketal (Figure 4A,B), which resembles glucose [74,75] and has high affinity for glucose transporters GLUT1 and GLUT3 (GLUT4 can be involved, but GLUT2 and GLUT5 are not) [54].”
From Vitamin C-Sources, Physiological Role, Kinetics, Deficiency, Use, Toxicity, and Determination (2021) · cites this paper as [74]
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- Authors
- Corpe, C. P., Lee, J.-H., Kwon, O., Eck, P., Narayanan, J., Kirk, K. L., & Levine, M.
- Affiliations
- National Institutes of Health (US)
- Corresponding author
- Levine, Mark
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 2005-02
- Volume
- 280
- Issue
- 7
- Pages
- 5211-5220
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W1996527523
- Cited by
- 95
- References
- 34
- Citations by year
- 2025: 3 · 2023: 5 · 2022: 5 · 2021: 6 · 2020: 9 · 2019: 4 · 2018: 4 · 2017: 5 · 2016: 2 · 2015: 2 · 2014: 4 · 2013: 12 · 2012: 7
- FWCI
- 4.81
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Nursing › Nutrition and Dietetics › Vitamin C and Antioxidants Research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Amino Acid Enzymes and Metabolism
- Health Sciences › Medicine › Oncology › Drug Transport and Resistance Mechanisms
- Keywords
- vitamin C transport, vitamin C, dehydroascorbic acid, SVCT1, SVCT2, GLUT1, GLUT3, Xenopus oocyte expression, human neutrophils, substrate specificity
- MeSH terms
- Animals, Ascorbic Acid, Biological Transport, Chromatography, High Pressure Liquid, Electron Spin Resonance Spectroscopy, Fibroblasts, Glucose, Humans, Kinetics, Monosaccharide Transport Proteins, Neutrophils, Oocytes, Oxidation-Reduction, Poly A, RNA, Messenger, Sodium, Xenopus laevis, Symporters, Organic Anion Transporters, Sodium-Dependent, Rats, Sodium-Coupled Vitamin C Transporters
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