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Cited by 458Vitamin C and Antioxidants ResearchAdvanced Synthetic Organic ChemistryOrganic Chemistry Synthesis Methods

Ascorbic Acid: Chemistry, Metabolism, and Uses

Paul A. Seib, Bert M. Tolbert·1982·Advances in Chemistry
DOI 10.1021/ba-1982-0200
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Abstract

The methods by which L-ascorbic acid has been synthesized are readily divided into three major categories. The first involves coupling a C1 fragment and a C5 fragment, and the second involves coupling a C2 fragment and a C4 fragment. The third involves the conversion of a C6 chain into the correct oxidation state and stereochemical configuration. All of these approaches will be reviewed with special regard given to those syntheses that are suitable for the preparation of analogues of L-ascorbic acid, the preparation of radiolabeled derivatives of L-ascorbic acid, and the current commercial synthesis of L-ascorbic acid.

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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 [75]

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Authors
Seib, P. A., & Tolbert, B. M.
ORCID
Paul A. Seib
Venue
Advances in Chemistry
Publisher
AMERICAN CHEMICAL SOCIETY
Published
1982-06-01
ISSN
0065-2393 (ISSN-L)
DOI
10.1021/ba-1982-0200
OpenAlex
W2499087708
Cited by
458
References
0
Citations by year
2026: 1 · 2025: 1 · 2024: 2 · 2023: 1 · 2022: 4 · 2021: 6 · 2020: 5 · 2019: 4 · 2018: 5 · 2017: 8 · 2016: 4 · 2015: 7 · 2014: 12 · 2013: 10 · 2012: 2
FWCI
13.36
Type
book
Language
en
Open access
closed
Locations
Advances in chemistry series (publishedVersion)
Topics
  • Health Sciences › Nursing › Nutrition and Dietetics › Vitamin C and Antioxidants Research
  • Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
  • Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
Keywords
vitamin C, ascorbic acid biosynthesis, ascorbic acid metabolism, stereochemical configuration, oxidation state

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