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A general and efficient approach to synthesize the phosphoramidites of 5'-18O labeled purine nucleosides.
Li, Nan-Sheng; Dai, Qing; Weissman, Benjamin; Harris, Michael E; Piccirilli, Joseph A.
Afiliación
  • Li NS; Department of Biochemistry & Molecular Biology, University of Chicago, Chicago, Illinois, USA.
  • Dai Q; Department of Chemistry, University of Chicago, Chicago, Illinois, USA.
  • Weissman B; Department of Chemistry, University of Chicago, Chicago, Illinois, USA.
  • Harris ME; Department of Chemistry, University of Florida, Gainesville, Florida, USA.
  • Piccirilli JA; Department of Biochemistry & Molecular Biology, University of Chicago, Chicago, Illinois, USA.
Nucleosides Nucleotides Nucleic Acids ; 42(11): 930-943, 2023.
Article en En | MEDLINE | ID: mdl-37233721
5'-18O labeled RNA oligos are important probes to investigate the mechanism of 2'-O-transphosphorylation reactions. Here we describe a general and efficient synthetic approach to the phosphoramidite derivatives of 5'-18O labeled nucleosides starting from the corresponding commercially available 5'-O-DMT protected nucleosides. Using this method, we prepared 5'-18O-guanosine phosphoramidite in 8 steps (13.2% overall yield), 5'-18O-adenosine phosphoramidite in 9 steps (10.1% overall yield) and 5'-18O-2'-deoxyguanosine phosphoramidite in 6 steps (12.8% overall yield). These 5'-18O labeled phosphoramidites can be incorporated into RNA oligos by solid phase synthesis for determination of heavy atom isotope effects in RNA 2'-O-transphosphorylation reactions.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Nucleósidos de Purina / Nucleósidos Idioma: En Revista: Nucleosides Nucleotides Nucleic Acids Asunto de la revista: BIOQUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos
Texto completo
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Nucleósidos de Purina / Nucleósidos Idioma: En Revista: Nucleosides Nucleotides Nucleic Acids Asunto de la revista: BIOQUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos