Citrulline is derived from the amino acid arginine during in vivo production of nitric oxide. Previous work in our laboratory has shown that fluorescent amino acids containing urea groups can serve as receptors for small inorganic anions like bicarbonate, dihydrogenphosphate, and chloride. A naphthalimide fluorophore was attached to the side-chain of Boc-Cit-OH via palladium(0)-catalyzed coupling under basic conditions, to afford Boc-Cit(naph)-OH. In acetonitrile solution, this compound shows modest affinity for Cl<sup>-</sup>. Efforts to extend the coupling protocol to accommodate base-sensitive Fmoc-Cit-OH, thereby giving a product suitable for modern solid-phase peptide synthesis, will be presented.

Anion binding by N-protected fluorescent citrulline

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.