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Experimental identification of aminomethanol (NH2CH2OH)-the key intermediate in the Strecker Synthesis.

ABSTRACT: The Strecker Synthesis of (a)chiral α-amino acids from simple organic compounds, such as ammonia (NH3), 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 (NH2CH2OH)- formed in the Strecker Synthesis to even the simplest amino acid glycine (H2NCH2COOH) has been elusive. Here, we report the identification of aminomethanol prepared in low-temperature methylamine (CH3NH2) - oxygen (O2) 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.

SUBMITTER: Singh SK 

PROVIDER: S-EPMC8770675 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Experimental identification of aminomethanol (NH<sub>2</sub>CH<sub>2</sub>OH)-the key intermediate in the Strecker Synthesis.

Singh Santosh K SK   Zhu Cheng C   La Jeunesse Jesse J   Fortenberry Ryan C RC   Kaiser Ralf I RI  

Nature communications 20220119 1

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 re  ...[more]

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