ArticleChemistry (Weinheim an der Bergstrasse, Germany)2024
A New Mechanism for Formation of Glycine from Glyoxylic Acid: the Aza-Cannizzaro Reaction.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- A quantum-chemical study of synthesis and stability of glycine on olivine surface.Journal of molecular modeling · 2026Article
- Non-targeted metabolomics reveals liver metabolome changes in broiler chickens fed diets supplemented with fermented brewer's grain.Scientific reports · 2026Article
- Influence of Rare Earth Elements on Prebiotic Reaction Networks Resembling the Biologically Relevant Krebs Cycle.Angewandte Chemie (International ed. in English) · 2026Article
- Elemental Trade-Off in the Selective Electro-Oxidation of Ethylene Glycol on Palladium-Silver/Nickel Electrodes.ChemSusChem · 2025Article
- From Amino Acids to α-Keto Acids via β-Elimination and Transamination Initiates a Pathway to Prebiotic Reaction Networks.Angewandte Chemie (International ed. in English) · 2025Article
- A New Mechanism for Formation of Glycine from Glyoxylic Acid: the Aza-Cannizzaro Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
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Authors and funding
3 authors.
Funding
Abstract
Glyoxylic acid and glycine are widely considered to have been important prebiotic building blocks. Several mechanistic routes have been previously examined for conversion of glyoxylic acid to glycine. Here we provide evidence for a new mechanistic path. Glycine is spontaneously formed from glyoxylic acid in ammonium-rich aqueous solutions at neutral pH; oxamic acid is generated as well. Hydride transfer from the glyoxylate-derived hemiaminal to the corresponding iminium ion appears to underlie this transformation. This proposed mechanism parallels the well-known Cannizzaro reaction mechanism, which leads us to suggest the designation "aza-Cannizzaro reaction." This discovery offers a new perspective on prebiotic nitrogen incorporation because glycine can be a source of nitrogen for more complex molecules, including other α-amino acids.
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