Journal article

Authors list: Paczelt, V; Wende, RC; Schreiner, PR; Eckhardt, AK

Publication year: 2023

Journal: Angewandte Chemie International Edition

Volume number: 62

Issue number: 11

ISSN: 1433-7851

eISSN: 1521-3773

Open access status: Hybrid

DOI Link: https://doi.org/10.1002/anie.202218548

Publisher: Wiley

Abstract: 
Simple unhindered aldimines tend to hydrolyze or oligomerize and are therefore spectroscopically not well characterized. Herein we report the formation and spectroscopic characterization of the simplest imino acid, namely glycine imine, by cryogenic matrix isolation IR and UV/Vis spectroscopy. Glycine imine forms after UV irradiation of 2-azidoacetic acid by N-2 extrusion in anti-(E,E)- and anti-(Z,Z)-conformation that can be photochemically interconverted. In matrix isolation pyrolysis experiments with 2-azidoacetic acid, glycine imine cannot be trapped as it further decarboxylates to aminomethylene. In aqueous solution glycine imine is hydrolyzed to hydroxy glycine and hydrated glyoxylic acid. At higher concentrations or in the presence of (FeSO4)-S-II as a reducing agent glycine imine undergoes self-reduction by oxidative decarboxylation chemistry. Glycine imine may be seen as one of the key reaction intermediates connecting prebiotic amino acid and sugar formation chemistry.

Harvard Citation style: Paczelt, V., Wende, R., Schreiner, P. and Eckhardt, A. (2023) Glycine Imine - The Elusive α-Imino Acid Intermediate in the Reductive Amination of Glyoxylic Acid, Angewandte Chemie International Edition, 62(11), Article e202218548. https://doi.org/10.1002/anie.202218548

APA Citation style: Paczelt, V., Wende, R., Schreiner, P., & Eckhardt, A. (2023). Glycine Imine - The Elusive α-Imino Acid Intermediate in the Reductive Amination of Glyoxylic Acid. Angewandte Chemie International Edition. 62(11), Article e202218548. https://doi.org/10.1002/anie.202218548