Year: 2024
Type: article
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.
Source: Chemistry - A European Journal
Institution: University of Wisconsin–Madison
Language: English
Subfield: Astronomy and Astrophysics
Field: Physics and Astronomy
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,640
Awards: New Foldamer Catalysts, G190310932, G3284659857, G4307208066, Laser-Enhanced NMR Instrumentation for Chemical and Biochemical Research, G5810665738, Graduate Research Fellowship Program (GRFP), MRI: Acquisition of an Operando 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer, G7514282927, QExactive (Orbitrap) mass spectrometer
OpenAlex ID: W4402971887