Improved Large-Scale Synthesis of Acridonylalanine for Diverse Peptide and Protein Applications.

ABSTRACT: Fluorescent unnatural amino acids give biochemists, biophysicists, and bioengineers new ways to probe the properties of proteins and peptides. Here, the synthesis of acridon-2-ylalanine (Acd) is optimized for large-scale production to enable ribosomal incorporation through genetic code expansion (GCE), and fluorenylmethoxycarbonyl (Fmoc)-protected Acd is prepared for solid-phase peptide synthesis (SPPS). We demonstrate the utility of Acd in several applications: first, Acd quenching by Tyr is used in the design of fluorescent protease sensors made by SPPS. Second, we demonstrate Acd incorporation into a lanthanide-binding peptide that is generated either by GCE or by SPPS and demonstrate the utility of Acd for sensitizing the emission of Eu³⁺. Finally, Acd is inserted into the i

SUBMITTER: Marmorstein JG 

PROVIDER: S-EPMC12443484 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature