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Cited by 128Origins and Evolution of LifeAdvanced Glycation End Products researchPhysical Organic Chemistry and Reaction Kinetics

The DOI matches its Crossref record; 48 of the 48 references it cites were found in a registry or an index.

The Sugar Model: Catalysis by Amines and Amino Acid Products

Weber, Arthur L.·2001·Origins of life and evolution of the biosphere
DOI 10.1023/a:1006750423942
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Abstract

Ammonia and amines (including amino acids) were shown to catalyze the formation of sugars from formaldehyde and glycolaldehyde, and the subsequent conversion of sugars to carbonylcontaining products under the conditions studied (pH 5.5 and 50 degrees C). Sterically unhindered primary amines were better catalysts than ammonia, secondary amines, and sterically hindered primary amines (i.e. alpha-aminoisobutyric acid). Reactions catalyzed by primary amines initially consumed formaldehyde and glycolaldehyde about 15-20 times faster than an uncatalyzed control reaction. The amine-catalyzed reactions yielded aldotriose (glyceraldehyde), ketotriose (dihydroxyacetone), aldotetroses (erythrose and threose), ketotetrose (erythrulose), pyruvaldehyde, acetaldehyde, glyoxal, pyruvate, glyoxylate, and several unindentified carbonyl products. The concentrations of the carbonyl products, except pyruvate and ketotetrose, initially increased and then declined during the reaction, indicating their ultimate conversion to other products (like larger sugars or pyruvate). The uncatalyzed control reaction yielded no pyruvate or glyoxylate, and only trace amounts of pyruvaldehyde, acetaldehyde and glyoxal. In the presence of 15 mM catalytic primary amine, such as alanine, the rates of triose and pyruvaldehyde of synthesis were about 15-times and 1200-times faster, respectively, than the uncatalyzed reaction. Since previous studies established that alanine is synthesized from glycolaldehyde and formaldehyde via pyruvaldehyde as its direct precursor, the demonstration that the alanine catalyzes the conversion of glycolaldehyde and formaldehyde to pyruvaldehyde indicates that this synthetic pathway is capable of autocatalysis. The relevance of this synthetic process, named the Sugar Model, to the origin of life is discussed.

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Research works printed but not linked: 4

  1. Bruice, T. C. and Benkovic, S. J.: 1966, Bioorganic Mechanisms, Vol. II, Benjamin, Inc., New York, pp. 186–199.
  2. Geissman, T. A.: 1944, 'The Cannizzaro Reaction', in R. Adams (ed.), Organic Reactions, Vol. II, John Wiley & Sons, New York, pp. 94–113.
  3. Grimmet, M. R.: 1965, Formation of Heterocyclic Compounds from Carbohydrates and Ammonia, Rev. Pure Appl. Chem. 15, 101–108.
  4. Jencks, W. P.: 1987, Catalysis on Chemistry and Enzumology, Dover Publications, New York, pp. 120–127.

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Metadata

Authors
Weber, A. L.
Affiliations
Ames Research Center (US)
Corresponding author
Weber, Arthur L.
Venue
Origins of life and evolution of the biosphere
Publisher
Springer Science and Business Media LLC
Published
2001-02
Volume
31
Issue
1-2
Pages
71-86
ISSN
  • 0169-6149 (ISSN-L)
  • 1573-0875
DOI
10.1023/a:1006750423942
OpenAlex
W1668230103
Cited by
127
References
48
Citations by year
2026: 3 · 2025: 4 · 2024: 4 · 2023: 4 · 2022: 5 · 2021: 1 · 2020: 5 · 2019: 1 · 2018: 2 · 2017: 4 · 2016: 5 · 2015: 5 · 2014: 3 · 2013: 5 · 2012: 2
FWCI
1.43
Type
journal article
Language
en
Open access
closed
Licence
Locations
  • Origins of Life and Evolution of Biospheres (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Clinical Biochemistry › Advanced Glycation End Products research
  • Physical Sciences › Chemistry › Organic Chemistry › Physical Organic Chemistry and Reaction Kinetics
Keywords
amine catalysis, formaldehyde, glycolaldehyde, sugar synthesis, methylglyoxal, alanine, autocatalysis, origin of life, prebiotic chemistry, glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, pyruvate, glyoxylic acid, glyoxal, acetaldehyde
MeSH terms
Origin of Life, Acetaldehyde, Amines, Amino Acids, Carbohydrates, Catalysis, Formaldehyde, Models, Chemical, Evolution, Molecular

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