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.
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Regioselective N1-ribosylation of hydantoin: synthesis and properties of the first contracted uridine analog.
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Department of Chemistry, Bar-Ilan University, Ramat-Gan 5290002, Israel.
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.
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