ALKYNE-CONTAINING AMIDOPHOSPHITE FOR THE FUNCTIONALIZATION OF SYNTHETIC OLIGONUCLEOTIDES AND A METHOD FOR ITS PRODUCTION Russian patent published in 2022 - IPC C07H21/00 C07C231/02 C12N15/09 

FIELD: organic chemistry and nucleic acid chemistry.

SUBSTANCE: inventions group relates to the field of organic chemistry and nucleic acid chemistry and is intended for the functionalization of synthetic oligonucleotides by the azide-alkyne cycloaddition method ("click chemistry"). Disclosed is a compound having the structural formula, where R1 is a protecting group that is stable under the conditions of oligonucleotide synthesis, selected from 4,4'-dimethoxytrityl (DMTr), 4-monomethoxytrityl (MMTr), trityl (Tr), trimethoxytrityl (TMTr), 9 -phenylxanthen-9-yl (Px), carbonate or silyl groups, R2 is hydrogen, methyl or ethyl, X is -O- or -NH-, and L is a -( CH₂)-n spacer group, where n = 1, 2 or 3; or -(CH₂CH₂O)_nCH₂-, where n = 1 or 2. Also disclosed is a method for preparing the above amidophosphite reagents, including the functionalization of the carboxyl group with linkers containing an alkyne group, followed by selective protection of one hydroxyl group and phosphitylation of the second hydroxyl group to obtain the target reagents with a total yield of 32-47%.

EFFECT: inventions group makes it possible to modify synthetic oligonucleotides in any position (3', 5' or inside) and when they are inserted, the natural internucleotide distance of 3 carbon atoms between phosphate groups is preserved.

9 cl, 5 ex