Reaction of Monosaccharides with Proteins: Possible Evolutionary Significance
Abstract
Measurements were made of the rate of condensation of various monosaccharides with amino groups of hemoglobin to form Schiff base linkages. The reactivity of each sugar was dependent on the extent to which it exists in the open (carbonyl) structure rather than in the ring (hemiacetal or hemiketal) structure. Among the 15 monosaccharides tested, aldoses showed higher reactivities than ketoses. Glucose was the least reactive of the aldohexoses. The emergence of glucose as the primary metabolic fuel may be due in part to the high stability of its ring structure which limits potentially deleterious nonenzymatic glycosylation of proteins.
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The rate for fructose-dependent intracellular formation of AGEs is 7.5-fold faster than that of glucose.
“It should be noted that glucose has the slowest rate in the glycation reaction of any sugar in cells while the rate for fructose-dependent intracellular formation of AGEs is 7.5-fold faster than that of glucose.[109]”
From The Role of Dietary Advanced Glycation End Products in Metabolic Dysfunction (2021) · cites this paper as [109]
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- Authors
- Bunn, H. F., & Higgins, P. J.
- Affiliations
- Brigham and Women's Hospital (US)
- Venue
- Science
- Published
- 1981-07-10
- Volume
- 213
- Issue
- 4504
- Pages
- 222-224
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2077088113
- Cited by
- 598
- References
- 27
- Citations by year
- 2026: 9 · 2025: 10 · 2024: 20 · 2023: 17 · 2022: 11 · 2021: 16 · 2020: 22 · 2019: 13 · 2018: 25 · 2017: 23 · 2016: 20 · 2015: 19 · 2014: 18 · 2013: 21 · 2012: 15
- FWCI
- 5.58
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Science (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Clinical Biochemistry › Advanced Glycation End Products research
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Carbohydrate Chemistry and Synthesis
- Keywords
- Schiff base formation, hemoglobin, glycation, aldoses, ketoses, glucose, aldohexoses
- MeSH terms
- Borohydrides, Glucose, Glycolysis, Glycosylation, Hemoglobin A, Hexoses, Humans, Monosaccharides, Schiff Bases, Evolution, Chemical, In Vitro Techniques
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