Synthesis of Fluorescent Dibenzofuran α-Amino Acids: Conformationally Rigid Analogues of Tyrosine

• DOI: 10.1021/acs.orglett.5c00433
• Publication Date: 2025-03-03T07:32:43Z
• Authors: Liyao Zeng; Olivia Marshall; Rochelle McGrory; Rebecca Clarke; Ryan J. Brown; Malcolm Kadodwala; Andrew R. Thomson; Andrew Sutherland
• Keywords: Dibenzofuran

We report two synthetic strategies for the preparation of dibenzofuran α-amino acids, expanding structural toolbox fluorescent probes. The involved synthesis via a Pd(II)-catalyzed C–O cyclization, alongside an efficient Negishi coupling approach faster access to analogues. These rigid tyrosine mimics possess enhanced properties compared proteinogenic amino acids as demonstrated by application lead compound FRET donor monitoring peptide hydrolysis serine protease.