Dynamic Formation of Imidazolidino Boronate Enables Design of Cysteine-Responsive Peptides.

We describe the dynamic and chemoselective conjugation between 2-formylphenylboronic acid and l-2,3-diaminopropionic acid yielding an imidazolidino boronate (IzB) complex. The IzB complex formation readily proceeds in biological milieu with little interference by common biomolecules except cysteine. We demonstrate the potential of this reversible conjugation for biological applications by creating "smart" peptides that specifically respond to cysteine in complex biological media. Specifically, the design and characterization of a fluorogenic sensor of cysteine is described.