title: Fluorous-assisted synthesis of (E)-5-[3-aminoallyl]-uridine-5'-O-triphosphate.
abstract: An efficient, reliable method for the chemical synthesis of (E)-5-[3-aminoallyl]-uridine-5'-O-triphosphate (AA-UTP), starting from 5-iodouridine, is described. This new strategy features the involvement of one-pot triphosphate formation and fluorous solid-phase extraction (F-SPE). The one-pot synthesis involves the mono phosphorylation of fluorous-tagged uridine, followed by the reaction with pyrophosphate to afford the fluorous-tagged AA-UTP. The F-SPE is achieved by installing a fluorous-tag onto the uridine prior to triphosphate formation, purification via F-SPE, and cleavage of the fluorous-tag. It is worth mentioning that this protocol produces AA-UTP in high yield and purity using one simple F-SPE; no conventional column chromatography is involved.
authors.affiliation: Life Sciences Solutions Group, Thermo Fisher Scientific, Austin, Texas.
authors.forename: Anilkumar R
authors.initials: AR
authors.lastname: Kore
authors.affiliation: Life Sciences Solutions Group, Thermo Fisher Scientific, Austin, Texas.
authors.forename: Bo
authors.initials: B
authors.lastname: Yang
authors.affiliation: Life Sciences Solutions Group, Thermo Fisher Scientific, Austin, Texas.
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Srinivasan
mesh_terms: D002845:Chromatography; D007065:Idoxuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D052616:Solid Phase Extraction / Q000379:methods*; D060327:Solid-Phase Synthesis Techniques; D014544:Uridine Triphosphate / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C035991:5-iodouridine; D007065:Idoxuridine; D014544:Uridine Triphosphate
keywords: fluorous separation; fluorous solid-phase extraction (F-SPE); nucleoside triphosphates; one-pot synthesis; phosphorylation