Synthesis and chelation study of a fluoroionophore and a glycopeptide based on an aza crown iminosugar structure

Capitalizing on a recently reported iminosugar-based aza-crown (ISAC) accessed by double Staudinger azaWittig coupling reaction, we have expanded the structural diversity of this new family sweet cyclam analogs. Replacement two secondary amines linking iminosugar units amide bonds obtained cyclodimerization with BOP and DIPEA led to macrocycle that did not demonstrate efficient Zn2+ chelation unlike parent ISAC. Introduction pyrene moieties ISAC yielded fluoroionophore selectively binds Hg2+ in methanol.