Formylpyrrole-based heterocycles for nucleic acid attachment to supports

A compound of Formula IV:

• wherein,
• W, X, Y, and Z are independently selected from the group consisting of CH, N, O, S, null, and bond;
• A is selected from the group consisting of aryl, hydrogen, hydroxyl, alkoxy hydroxyalkyl, and a C1-C4 straight chain or branched alkyl;
• Q is an aldehyde or protected aldehyde;
• wherein the bonds between each of W-X, X-Y, and Y-Z are selected from the group consisting of single bond, double bond, a triple bond, and no bond when W, X, Y, or Z is a bond;
• L is a linker selected from a C1-C12 alkyl, aralkyl, and aryl, any of which is optionally substituted;
• wherein one or more methylene unit (CH2) unit of said C1-C12 alkyl is optionally replaced by any combination of oxygen, carbonyl(C═O), and NH;
• and
• Nu is a nucleic acid.

A support-bound nucleic acid of Formula V:

• wherein,
• W, X, Y, and Z are independently selected from the group consisting of CH, N, O, S, null, and bond;
• A is selected from the group consisting of aryl, hydrogen, hydroxyl, alkoxy hydroxyalkyl, and a C1-C4 straight chain or branched alkyl;
• Q is an aldehyde (alkene) or protected aldehyde;
• wherein the bonds between each of W-X, X-Y, and Y-Z are selected from the group consisting of single bond, double bond, a triple bond, and no bond when W, X, Y, or Z is a bond;
• L is a linker selected from a C1-C12 alkyl, aralkyl, and aryl, any of which is optionally substituted;
• wherein one or more methylene unit (CH2) unit of said C1-C12 alkyl is optionally replaced by any combination of oxygen, carbonyl(C═O), and NH;
• Nu is a nucleic acid;
• Su is a support material;
• and
• B is a single or double bond, such that when B is a single bond, R is hydrogen and when B is a double bond R is null.

A method of immobilizing a nucleic acid comprising forming a Schiff-base product by reaction of a compound of Formula IV:

• wherein,
• W, X, Y, and Z are independently selected from the group consisting of CH, N, O, S, null, and bond;
• A is selected from the group consisting of aryl, hydrogen, hydroxyl, alkoxy hydroxyalkyl, and a C1-C4 straight chain or branched alkyl;
• Q is an aldehyde (alkene) or protected aldehyde;
• wherein the bonds between each of W-X, X-Y, and Y-Z are selected from the group consisting of single bond, double bond, a triple bond, and no bond when W, X, Y, or Z is a bond;
• L is a linker selected from a C1-C12 alkyl, aralkyl, and aryl, any of which is optionally substituted;
• wherein one or more methylene unit (CH2) unit of said C1-C12 alkyl is optionally replaced by any combination of oxygen, carbonyl(C═O), and NH;
• and
• Nu is a nucleic acid;
• with a support material displaying an amino or masked amino functional group.