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Efficient Desulfurization of 2-Thiopyrimidine Nucleosides to the Corresponding 4-Pyrimidinone Analogues Using Trans-2-(phenylsulfonyl)-3-phenyloxaziridine by Elżbieta Sochacka; Iwona Frątczak is a Chemistry article available to read on EtoBox.
What is Efficient Desulfurization of 2-Thiopyrimidine Nucleosides to the Corresponding 4-Pyrimidinone Analogues Using Trans-2-(phenylsulfonyl)-3-phenyloxaziridine about?
A brief treatment of 2-thiopyrimidine nucleosides (s 2 U \* ) with trans-2-phenylsulfonyl-3-phenyloxaziridine (PSO) results in efficient substrate desulfurization leading to the corresponding 4-pyrimidinone analogues (H 2 U \* ). The key transformation proceeds through oxidation of the 2-thiocarbonyl group to a sulfur oxyacid derivative and subsequent elimination of sulfur dioxide. 4-Pyrimidinone 1-b-D D-riboside (H 2 U) has been transformed into the respective phosphoramidite, a ready-to-use monomer for the introduction of a modified nucleoside into an oligonucleotide chain. Moreover, the effective desulfurization of the 2-thiouridine nucleotide could be achieved directly at the oligonucleotide level, by treatment of the TdA(s 2 U)dGdC oligonucleotide with PSO, as verified by MALDI-TOF mass spectrometry.
Who reads Efficient Desulfurization of 2-Thiopyrimidine Nucleosides to the Corresponding 4-Pyrimidinone Analogues Using Trans-2-(phenylsulfonyl)-3-phenyloxaziridine?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Elżbieta Sochacka; Iwona Frątczak
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)
- Published
- 2004
- Language
- EN
- Field
- Chemistry (Physical Sciences)