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

Odai Bsoul; Yakir Lampel; Maayan Rofe; Natalie Pariente-Cohen; Chen Timsit; Bilha Fischer

doi:10.1039/d4cc06033d

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

Odai Bsoul
, Yakir Lampel
, Maayan Rofe
, Natalie Pariente-Cohen
, Chen Timsit
, Bilha Fischer

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

Abstract

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 Vorbr_üggen reaction. We report synthetic routes and explore HR features such as acidity, stability, base pairing/stacking, and crystal/solution conformation compared to uridine.

Original language	English
Pages (from-to)	2281-2284
Number of pages	4
Journal	Chemical Communications
Volume	61
Issue number	11
DOIs	https://doi.org/10.1039/d4cc06033d
State	Published - 30 Jan 2025

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Publisher Copyright:
© The Royal Society of Chemistry 2025.

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10.1039/d4cc06033d

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AU - Timsit, Chen

AU - Fischer, Bilha

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

Abstract

Bibliographical note

UN SDGs

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