Synthesis of Oligonucleotides Carrying Inter-nucleotide N -(Benzoazole)-phosphoramide Moieties.

Academic Journal

Vasilyeva SV; Institute of Chemical Biology and Fundamental Medicine, SB of RAS, pr. Lavrent'eva 8, 630090 Novosibirsk, Russia.
Baranovskaya EE; Institute of Chemical Biology and Fundamental Medicine, SB of RAS, pr. Lavrent'eva 8, 630090 Novosibirsk, Russia.
Dyudeeva ES; Institute of Chemical Biology and Fundamental Medicine, SB of RAS, pr. Lavrent'eva 8, 630090 Novosibirsk, Russia.
Lomzov AA; Institute of Chemical Biology and Fundamental Medicine, SB of RAS, pr. Lavrent'eva 8, 630090 Novosibirsk, Russia.
Pyshnyi DV; Institute of Chemical Biology and Fundamental Medicine, SB of RAS, pr. Lavrent'eva 8, 630090 Novosibirsk, Russia.

ACS omega [ACS Omega] 2022 Dec 21; Vol. 8 (1), pp. 1556-1566. Date of Electronic Publication: 2022 Dec 21 (Print Publication: 2023).

English

In this work, we present new oligonucleotide derivatives containing inter-nucleotide N -benzimidazole, N -benzoxazole, N -benzothiazole, and 1,3-dimethyl- N -benzimidazole (benzoazoles) phosphoramide groups. These modifications were introduced via the Staudinger reaction with appropriate azides during standard automated solid-phase oligonucleotide synthesis. The principal structural difference between the new azido modifiers and those already known is that they are bulk heterocyclic structures, similar to purine nucleoside bases. Modified oligonucleotides with one and two modifications at different positions and multiple modified heteronucleotide sequences were obtained with high yields. The possibility of multiple modifications in the process of automatic DNA synthesis is fundamental and critical for further application of our oligonucleotide derivatives. Initial studies on the properties of new oligonucleotides were carried out. The stability of the oligodeoxyribonucleotide duplex containing phosphoramide groups of N -benzoazoles with complementary DNA or RNA is slightly lower than that of native complexes.
Competing Interests: The authors declare no competing financial interest.
(© 2022 The Authors. Published by American Chemical Society.)