ol7b03116_si_001.pdf (2.13 MB)
Dynamic Formation of Imidazolidino Boronate Enables Design of Cysteine-Responsive Peptides
journal contribution
posted on 2017-12-20, 21:05 authored by Kaicheng Li, Chelsea Weidman, Jianmin GaoWe
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.