61707-84-4Relevant academic research and scientific papers
Compositions and Methods for Reverse Automated Nucleic Acid Synthesis
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Paragraph 0102-0103, (2019/10/29)
Methods for reverse automated nucleic acid synthesis, and 5′-H-phosphonates suitable for use in the same, as well as methods for making 5′-H-phosphonates, are described.
Photochemical generation and reactivity of the 5,6-dihydrouridin-6-yl radical
Newman, Cory A.,Resendiz, Marino J. E.,Sczepanski, Jonathan T.,Greenberg, Marc M.
experimental part, p. 7007 - 7012 (2009/12/24)
(Chemical Equation Presented) Nucleobase radicals are the major family of reactive intermediates formed when nucleic acids are exposed to hydroxyl radical, which is produced by γ-radiolysis and Fe·EDTA. Significant advances have been made in understanding the role of nucleobase radicals in oxidative DNA damage by independently generating these species from photochemical precursors. However, this approach has been used much less frequently to study RNA molecules. Norrish type I photocleavage of the tert-butyl ketone (2b) enabled studying the reactivity of 5′-benzoyl-5,6- dihydrouridin-6-yl (1b). High mass balances were observed under aerobic or anaerobic conditions, and O2 did not affect the photochemical conversion of the ketone (2b) to 1b. Competition studies with O2 indicate that the radical abstracts hydrogen atoms from β-mercaptoethanol with a bimolecular rate constant = 2.6 ± 0.5 × 106 M-1s-1. The major product formed in the presence of O 2 was 5′-benzoyl-6-hydroxy-5,6-dihydrouridine (6). In contrast, 5-benzoyl-ribonolactone (7), a hypothetical product resulting from C1′-hydrogen atom abstraction by the peroxyl radical, could not be detected. Overall, tert-butyl ketone 2b is a clean source of 5′-benzoyl-5,6-dihydrouridin-6-yl (1b) and should prove useful for studying the reactivity of the respective radical in RNA.
The chemistry of 2′,3′-seconucleosides IV. Synthesis and reactions of 3′-azido-2′,3′-dideoxy-2′,3′- secothymidine and related analogues
Kumar, Ajit,Walker, Richard T.
, p. 3101 - 3110 (2007/10/02)
The synthesis of a series of 2,3-seconucleoside analogues related to nucleosides previously shown to possess anti-HIV activity is described. Using strategies to distinguish between the three primary hydroxyl groups of a 2,3-seconucleoside, 3-azido-2,3-dideoxy-2,3-secothymidine and 2,3-dideoxy-2,3-secothymidine have been prepared. These compounds, several of the intermediates in their synthesis, as well as O22-anhydro-3-azido-3-deoxy-2,3-secothymidine and several 2,3-secouridine analogues have been tested for their ability to prevent infection of cells by HIV. None showed any significant toxicity or antiviral activity.
