Synthesis of β-Pyridyl α-Amino Acids: Conformationally Sensitive Charge Transfer-Based Fluorophores.

ABSTRACT: Unnatural α-amino acids with charge transfer-based poly aromatic side chains have been designed as conformationally sensitive fluorophores. These were prepared using a hetero-Diels-Alder reaction and a Knoevenagel-Stobbe process to generate a biaryl pyridyl unit, followed by iron-catalyzed bromination and a Suzuki-Miyaura cross-coupling reaction to complete the triaryl system. A photophysical study led to the discovery of a p-methoxy analogue which exhibited viscosity-sensitive fluorescence in which emission could be controlled between twisted and planar conformations.

SUBMITTER: Riley LM 

PROVIDER: S-EPMC11217948 | biostudies-literature | 2024 Jun

REPOSITORIES: biostudies-literature