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Updated: Jul 15, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Preparation of potential cell-permeant nucleoside-2',3'-cyclic phosphate precursors
Simone Battaggia1, Emma E Smith, Joseph S Vyle
1School of Chemistry and Chemical Engineering, Queen's University Belfast, Belfast, United Kingdom.
Abstract:
Uridine-3'-phosphorothiolate triesters bearing lipophilic moieties were prepared via Michaelis-Arbuzov chemistry. Subsequent deprotection of the S-cholesteryl phosphorothiolate triester afforded the corresponding diester which underwent spontaneous Cyclization to cleanly afford uridine 2',3'-cyclic phosphate. This transesterification reaction could be expedited by treatment with iodine under mild, neutral conditions.
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