Bioconjugation of macromolecules
AssigneeProligo LLC
InventorsWolfgang Pieken, Ken Hill, Bruce Eaton, Danny McGee, Kurt Vagle, Larry Gold, Andrew Stephens
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Abstract
This invention discloses a novel method for conjugating macromolecules to other molecular entities. Specifically, this invention discloses a method for conjugating or derivatizing macromolecules, such as oligonucleotides and proteins, using cycloaddition reactions, such as the Diels-Alder reaction or 1,3-dipolar cycloadditions. Included in the invention are the novel bioconjugated macromolecules that can be prepared according to the method of the invention.
Claims19
A method for bioconjugating macromolecules comprising the step of reacting a macromolecule derivatized with a moiety capable of undergoing a cycloaddition reaction, wherein said macromolecule is selected from the group consisting of nucleic acids, oligonucleotides, proteins, peptides, carbohydrates, polysaccharides, glycoproteins, lipids, hormones, drugs and prodrugs with a molecular entity derivatized with a moiety capable of reacting with said derivatized macromolecule via a cycloaddition reaction, wherein said derivatized macromolecule and said derivatized molecular entity are unassociated.
A compound selected from the group of compounds having the following structure:
- wherein
- B is a nucleobase;
- A and A′ are 2′-sugar substituents;
- W is independently selected from the group consisting of a nucleotide, an oligonucleotide having between 2-1000 nucleobases, or H;
- and
- X is a diene, dienophile, 1,3-dipolarophile, 1,3-dipole or other moiety capable of undergoing a cycloaddition reaction additionally, when X is attached to the nucleobase B it can be attached to a carbon atom, an exocyclic nitrogen or an exocyclic oxygen.
A derivatized oligonucleotide selected from the group consisting of:
- wherein W is independently selected from a nucleotide or an oligonucleotide having between 2-1000 nucleobases.
A compound selected from the group consisting of:
- wherein
- B is a nucleobase.
Dependencies are inferred from the claim text.