Regioselective N1-ribosylation of hydantoin: synthesis and properties of the first contracted uridine analog.

Modified nucleosides are vital in mRNA vaccines. We developed a contracted uridine analog, N1-hydantoinyl-ribose, HR, using steric shields to invert the regioselectivity of the classic Vorbrüggen reaction. We report synthetic routes and explore HR features such as acidity, stability, base pairing/stacking, and crystal/solution conformation compared to uridine.

Aminomethylene-Phosphonate Analogue as a Cu(II) Chelator: Characterization and Application as an Inhibitor of Oxidation Induced by the Cu(II)-Prion Peptide Complex.

Recently, we reported on a series of aminomethylene-phosphonate (AMP) analogues, bearing one or two heterocyclic groups on the aminomethylene moiety, as promising Zn(II) chelators. Given the strong Zn(II) binding properties of these compounds, they may find useful applications in metal chelation therapy. With a goal of inhibiting the devastating oxidative damage caused by prion protein in prion diseases, we explored the most promising ligand, {bis[(1-imidazol-4-yl)methyl]amino}methylphosphonic acid, AMP-(Im), , as an inhibitor of the oxidative reactivity associated with the Cu(II) complex of prion peptide fragment 84-114.