New phosphorylating reagents 1 and 2 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 and 2) 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/H2O solution. Due to this one-pot treatment, it is possible to use the phosphorylating reagents (1 and 2) for the synthesis of base-sensitive ODNs. The reagents 1 and 2 are unique among phosphorylating reagents.
New phosphorylating reagents for deoxyribonucleosides and oligonucleotides / Romanucci, Valeria; Zarrelli, Armando; Guaragna, Annalisa; DI MARINO, Cinzia; DI FABIO, Giovanni. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 58:12(2017), pp. 1227-1229. [10.1016/j.tetlet.2017.02.034]
New phosphorylating reagents for deoxyribonucleosides and oligonucleotides
ROMANUCCI, VALERIA;ZARRELLI, ARMANDO;GUARAGNA, ANNALISA;DI MARINO, CINZIA;DI FABIO, GIOVANNI
2017
Abstract
New phosphorylating reagents 1 and 2 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 and 2) 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/H2O solution. Due to this one-pot treatment, it is possible to use the phosphorylating reagents (1 and 2) for the synthesis of base-sensitive ODNs. The reagents 1 and 2 are unique among phosphorylating reagents.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
