Access to N-α-deuterated amino acids and DNA conjugates via Ca(II)-HFIP-mediated reductive deutero-amination of α-oxo-carbonyl compounds.

ABSTRACT: The development of practical and selective strategies for deuterium incorporation to construct deuterated molecules, particularly deuterium-labeled amino acids, has become as a growing focus of basic research, yet it remains a formidable challenge. Herein, we present a bioinspired calcium-HFIP-mediated site-selective reductive deutero-amination of α-oxo-carbonyl compounds with amines. Utilizing d₂-Hantzsch ester as the deuterium source, this reaction attains remarkable deuteration efficiency (> 99% deuteration). It enables the synthesis of N-α-deuterated amino acid motifs with a wide range of functionality, as evidenced by over 130 examples. The method exhibits compatibility with diverse substrates, such as amino acids, peptides, drug molecules, and natural products bearing diff

SUBMITTER: Li H 

PROVIDER: S-EPMC11842556 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature