Replication Data for: Photochemical Generation and Characterization of Alanine Imine: A Key Intermediate in Prebiotic Amino Acid Formation

Simple imino acids have received sparse consideration as reactive intermediates in the formation of amino acids under plausible prebiotic or astrochemical conditions. 2 azidopropionic acid decomposes after UV irradiation under cryogenic matrix isolation conditions to dinitrogen and 2 iminopropionic acid, namely alanine imine, which is the proposed key intermediate in biological relevant alanine transaminase reactions.

Three conformers of alanine imine were spectroscopically characterized by IR and UV/Vis spectroscopy in solid argon at 3 K. One high-energy conformer can be selectively prepared by the near infrared 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 intermediately formed imine intermediates as identified by 1H-NMR spectroscopy.