New phosphorylating reagents for deoxyribonucleosides and oligonucleotides. Issue 12 (22nd March 2017)

• Record Type: Journal Article
• Authors: Romanucci, Valeria; Zarrelli, Armando; Guaragna, Annalisa; Di Marino, Cinzia; Di Fabio, Giovanni
• Is Part Of: Tetrahedron letters. Volume 58:Issue 12(2017)
• Page Start: 1227
• Page End: 1229
• Publication Date: 2017-03-22
• Subjects: Phosphorylation -- Phosphate protecting group -- Nucleotides -- Oligonucleotides -- Solid phase synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.02.034
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: New phosphorylating reagents. New phosphate protecting group. Synthesis of Nucleotides and Oligonucleotides by Solid phase synthesis. Abstract: New phosphorylating reagents1 and2 were prepared in three steps from 4-hydroxybenzaldehyde. They showed good efficiency in the solid phase synthesis of 5′-phosphate monoester nucleosides. End-phosphate DNA sequence synthesis demonstrated the efficiency of the new reagents (1 and2 ) according to the general procedure of automated DNA synthesis. The oxidation of P(III) to P(V) and the removal of benzyl protecting groups were achieved in a single step by treatment with a 0.02 M I2 /pyridine/H2 O solution. Due to this one-pot treatment, it is possible to use the phosphorylating reagents (1 and2 ) for the synthesis of base-sensitive ODNs. The reagents1 and2 are unique among phosphorylating reagents.