Drabkin, Vladimir D;
Thiehoff, Christian;
Sandoval-Salinas, María Eugenia;
Paczelt, Viktor;
Crespo-Otero, Rachel;
Eckhardt, André K;
(2025)
Photochemical Generation and Characterization of Alanine Imine: A Key Intermediate in Prebiotic Amino Acid Formation.
Journal of the American Chemical Society
, Article jacs.5c14327. 10.1021/jacs.5c14327.
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Abstract
Simple imino acids have received sparse consideration as reactive intermediates in the formation of amino acids under prebiotic or astrochemical conditions. Under cryogenic matrix isolation conditions, 2-azidopropionic acid decomposes after ultraviolet (UV) irradiation to dinitrogen and 2-iminopropionic acid, namely, alanine imine, which is the proposed key intermediate in biologically relevant alanine transaminase reactions. Three conformers of alanine imine were spectroscopically characterized by Fourier transform infrared (FT-IR) and ultraviolet-visible (UV/vis) spectroscopy in solid argon at 3.5 K. One high-energy conformer can be selectively prepared by the near-IR induced excitation of an OH-overtone vibration. In the dark, this conformer undergoes H-tunneling CO-bond rotamerization. In aqueous solution, 2-azidopropionic acid decomposes to glyoxylic and pyruvic acid after hydrolysis of the formed imine intermediates as identified by 1H NMR spectroscopy. Under more acidic conditions and prolonged irradiation, the intermediary formed imino acids are reduced to their glycine and alanine amino acid equivalents, respectively.
| Type: | Article |
|---|---|
| Title: | Photochemical Generation and Characterization of Alanine Imine: A Key Intermediate in Prebiotic Amino Acid Formation |
| Location: | United States |
| DOI: | 10.1021/jacs.5c14327 |
| Publisher version: | https://doi.org/10.1021/jacs.5c14327 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10215746 |
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