New Zwitter-Ionic Oligonucleotides: Preparation and Complementary Binding

Patrushev, D E; Буракова, Е. А.; Bizyaev, S. N.; Фокина, А. А.; Stetsenko, Dmitry A.

doi:10.1134/s0026893323020164

Cited by 1 publication

(1 citation statement)

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“…The fully modified oligonucleotide conjugate D6 with 1,1-dimethylethylenediamine residue at each internucleotidic position demonstrated a significant increase in retention time compared to the singly modified conjugate D5 (Figure 4A). In turn, the singly modified conjugate D5 showed a small decrease in the retention time compared to the unmodified control, presumably due to the presence of a polar zwitterionic group [83], but this effect was not observed for the 5 ′ -dimethoxytritylated D7 (Figure 4B). The separation of the main peak into the peaks of diastereomers was detected only for the fully modified D6 and D7, which are the mixtures of 32 stereoisomers due to the presence of a chiral center at each of the five internucleotidic positions.…”

Section: Resultsmentioning

confidence: 96%

A Convenient Oligonucleotide Conjugation via Tandem Staudinger Reaction and Amide Bond Formation at the Internucleotidic Phosphate Position

Klabenkova,

Zhdanova,

Burakova

et al. 2024

IJMS

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Staudinger reaction on the solid phase between an electronodeficit organic azide, such as sulfonyl azide, and the phosphite triester formed upon phosphoramidite coupling is a convenient method for the chemical modification of oligonucleotides at the internucleotidic phosphate position. In this work, 4-carboxybenzenesulfonyl azide, either with a free carboxy group or in the form of an activated ester such as pentafluorophenyl, 4-nitrophenyl, or pentafluorobenzyl, was used to introduce a carboxylic acid function to the terminal or internal internucleotidic phosphate of an oligonucleotide via the Staudinger reaction. A subsequent treatment with excess primary alkyl amine followed by the usual work-up, after prior activation with a suitable peptide coupling agent such as a uronium salt/1-hydroxybenzotriazole in the case of a free carboxyl, afforded amide-linked oligonucleotide conjugates in good yields including multiple conjugations of up to the exhaustive modification at each phosphate position for a weakly activated pentafluorobenzyl ester, whereas more strongly activated and, thus, more reactive aryl esters provided only single conjugations at the 5′-end. The conjugates synthesized include those with di- and polyamines that introduce a positively charged side chain to potentially assist the intracellular delivery of the oligonucleotide.

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Section: Resultsmentioning

confidence: 96%