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Photo-On-Demand Synthesis of α-Amino Acid N-Carboxyanhydrides with Chloroform.

ABSTRACT: Amino acid N-carboxyanhydrides (NCAs) are conventionally synthesized from α-amino acids and phosgene. The present study reports in situ photo-on-demand phosgenation reactions of amino acids with CHCl₃ for synthesizing NCAs. A series of NCAs were obtained on a gram scale upon photo-irradiation of a mixture solution of CHCl₃ and CH₃CN containing an amino acid at 60-70 °C under O₂ bubbling. This method presents a safe and convenient reaction controlled by light without special apparatuses and reagents.

SUBMITTER: Sugimoto T

PROVIDER: S-EPMC9631898 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Photo-On-Demand Synthesis of α-Amino Acid N-Carboxyanhydrides with Chloroform.

Sugimoto Toshiyuki T Kuwahara Tomoya T Liang Fengying F Wang Huirong H Tsuda Akihiko A

ACS omega 20221019 43

Amino acid N-carboxyanhydrides (NCAs) are conventionally synthesized from α-amino acids and phosgene. The present study reports in situ photo-on-demand phosgenation reactions of amino acids with CHCl3 for synthesizing NCAs. A series of NCAs were obtained on a gram scale upon photo-irradiation of a mixture solution of CHCl3 and CH3CN containing an amino acid at 60-70 °C under O2 bubbling. This method presents a safe and convenient reaction contro ...[more]

PMID: 36340075

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