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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

All Science Journal Classification (ASJC) codes

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d4cc06033d

Cite this

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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{\"u}ggen 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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AU - Rofe, Maayan

AU - Pariente-Cohen, Natalie

AU - Timsit, Chen

AU - Fischer, Bilha

PY - 2025/1/30

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AB - 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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U2 - 10.1039/d4cc06033d

DO - 10.1039/d4cc06033d

M3 - مقالة

C2 - 39803794

SN - 1359-7345

VL - 61

SP - 2281

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JO - Chemical Communications

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ER -

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

Abstract

UN SDGs

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