TY - JOUR
T1 - Regioselective N1-ribosylation of hydantoin
T2 - synthesis and properties of the first contracted uridine analog
AU - Bsoul, Odai
AU - Lampel, Yakir
AU - Rofe, Maayan
AU - Pariente-Cohen, Natalie
AU - Timsit, Chen
AU - Fischer, Bilha
N1 - Publisher Copyright:
© The Royal Society of Chemistry 2025.
PY - 2025/1/30
Y1 - 2025/1/30
N2 - 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.
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.
UR - https://www.scopus.com/pages/publications/85215655710
U2 - 10.1039/d4cc06033d
DO - 10.1039/d4cc06033d
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C2 - 39803794
AN - SCOPUS:85215655710
SN - 1359-7345
VL - 61
SP - 2281
EP - 2284
JO - Chemical Communications
JF - Chemical Communications
IS - 11
ER -
