Reusable solid support for oligonucleotide synthesis,...

C - Chemistry – Metallurgy – 07 – H

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C07H 23/00 (2006.01) C07H 19/06 (2006.01) C07H 19/16 (2006.01) C07H 21/00 (2006.01)

Patent

CA 2241331

A solid support for oligonucleotide synthesis is disclosed. The solid support has formula (1) wherein: R8 is selected from the group consisting of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C30 aryl group and a substituted or unsubstituted C5-C40 alkylaryl group; X3 and X4 are the same or different and are selected from the group consisting of -O-, -S-, -S(O)2- and -N(R12)-; R12 is selected from the group consisting of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C5-C30 aryl group and a substituted or unsubstituted C5-C40 alkylaryl group; and Y is selected from the group consisting of: -CH2-CH2-; -CH2-; -CH2-O-CH2-; -CH2-CH2-CH2-; -CH=CH-; - CH=C(CH3)-; -C(CH3)=C(CH3)-; -CH2-C(=CH2)-; and -CH2-S-CH2-; wherein when Y is -CH2-CH2-, at least one of X3 and X4 is -O-. An aspect of the invention also relates to a linker arm for oligonucleotide synthesis based on the solid support. Process for producing of the solid support and the linker arm, respectively, are also disclosed. The linker arm is characterized by being reusable in an otherwise conventional oligonucleotide production protocol.

L'invention concerne un support solide pour la synthèse d'oligonucléotides. Le support solide a la formule (1). Dans cette formule, R?8¿ est un groupe C¿1?-C¿20? alkyle substitué ou non, un groupe C¿5?-C¿30? aryle substitué ou non ou un groupe C¿5?-C¿40? alkylaryle substitué ou non; X?3¿ et X?4¿ sont les mêmes ou différents et ce sont -O-, -S-, -S(O)¿2?- ou -(N(R?12¿)-; R?12¿ est un groupe C¿1?-C¿20? alkyle substitué ou non, un groupe C¿5?-C¿30? aryle substitué ou non ou un groupe C¿5?-C¿40? alkylaryle substitué ou non; et Y est -CH¿2?-CH¿2?-; -CH¿2?-; -CH¿2?-O-CH¿2?-; -CH¿2?-CH¿2?-CH¿2?-; -CH=CH-; -CH=C(CH¿3?)-; -C(CH¿3?)=C(CH¿3?)-; -CH¿2?-C(=CH¿2?)-; and -CH¿2?-S-CH¿2?-; où quand Y est -CH¿2?-CH¿2?-, au moins un d'entre X?3¿ et X?4¿ est -O-. L'invention concerne également un bras de liaison fixé sur un support solide, pour la synthèse d'oligonucléotides. L'invention concerne en outre un procédé pour fabriquer le support solide et le bras de liaison. Le bras de liaison est caractérisé par le fait qu'il est réutilisable dans ce procédé de synthèse d'oligonucléotides qui, par ailleurs, est un procédé tout à fait classique.

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