Synthesis and Fluorescent Properties of Alkynyl- and Alkenyl-Fused Benzotriazole-Derived α-Amino Acids.

ABSTRACT: Fluorescent unnatural α-amino acids are widely used as probes in chemical biology and medicinal chemistry. While a variety of structural classes have been developed, there is still a requirement for new environmentally sensitive analogues that can closely mimic proteinogenic α-amino acids. Here, we report the synthesis and fluorescent properties of highly conjugated, benzotriazole-derived α-amino acids designed to mimic l-tryptophan. Alkynyl-substituted analogues were prepared using three key steps, nucleophilic aromatic substitution with a 3-aminoalanine derivative, benzotriazole formation via a one-pot diazotization and cyclization process, and a Sonogashira cross-coupling reaction. E-Alkenyl-substituted benzotriazoles were accessed by stereoselective partial hydrogenation

SUBMITTER: Riley LM 

PROVIDER: S-EPMC9942204 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature