Synthesis of a new fluorescent macrocyclic α-amino acid derivative via tandem cross-enyne/ring-closing metathesis cascade catalyzed by ruthenium based catalysts

A simple methodology to a unique macrocyclic α-amino acid (AAA) derivative involving three step synthetic sequence has been reported. In addition, various ruthenium based catalysts were studied to enhance the selectivity of the desired macrocyclic AAA derivative 6. The fluorescence behavior of these AAA derivatives 5 and 6 indicate their potential applications in biological sciences as biomarkers, ion sensors and peptidomimetics.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Synthesis of a novel macrocyclic α-amino acid derivative via tandem metathesis, first of its kind. ► Simple methodology to a unique macrocyclic α-amino acid (AAA) derivative in just three steps. ► Various ruthenium based catalysts were studied to improve the selectivity in cross-enyne metathesis. ► Fluorescence behavior of these AAA derivatives indicate their potential applications in biological. sciences such as biomarkers, ion sensors and peptidiomemetics