Experimental identification of aminomethanol (NH<sub>2</sub>CH<sub>2</sub>OH)-the key intermediate in the Strecker Synthesis.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 35046418.
- Also identified by DOI 10.1038/s41467-022-27963-z and PMC identifier 8770675.
- Licence recorded as CC BY.
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Abstract
The Strecker Synthesis of (a)chiral α-amino acids from simple organic compounds, such as ammonia (NH<sub>3</sub>), aldehydes (RCHO), and hydrogen cyanide (HCN) has been recognized as a viable route to amino acids on primordial earth. However, preparation and isolation of the simplest hemiaminal intermediate - the aminomethanol (NH<sub>2</sub>CH<sub>2</sub>OH)- formed in the Strecker Synthesis to even the simplest amino acid glycine (H<sub>2</sub>NCH<sub>2</sub>COOH) has been elusive. Here, we report the identification of aminomethanol prepared in low-temperature methylamine (CH<sub>3</sub>NH<sub>2</sub>) - oxygen (O<sub>2</sub>) ices upon exposure to energetic electrons. Isomer-selective photoionization time-of-flight mass spectrometry (PI-ReTOF-MS) facilitated the gas phase detection of aminomethanol during the temperature program desorption (TPD) phase of the reaction products. The preparation and observation of the key transient aminomethanol changes our perception of the synthetic pathways to amino acids and the unexpected kinetic stability in extreme environments.