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US 2026/0028320 A1Published application
Reagents and methods for bioorthogonal labeling of biomolecules in living cells
AssigneeOregon State University
InventorsRyan A. Mehl, Robert Blizzard
Life of this patent
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Abstract
Tetrazine non-canonical amino acids, methods for genetic encoding proteins and polypeptides using the tetrazine amino acids, proteins and polypeptides comprising the tetrazine amino acids, and compositions comprising the proteins and polypeptides having at least one post-translational modification thereof comprising in vivo reaction with the incorporated tetrazine amino acid and a second molecule.
Claims14
A protein or polypeptide comprising:
- at least one tetrazine amino acid residue, wherein the tetrazine amino acid residue is derived from a compound having the formula:
- or a stereoisomer or salt thereof, wherein:
- R is selected from substituted or unsubstituted C1-C6 alkyl group and substituted or unsubstituted phenyl group;
- Ra, Rb, Rc, and Rd are independently selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and halo;
- RC is hydrogen, a counter ion, or a carboxyl protecting group;
- and
- RN is hydrogen or an amine protecting group.
4 more elements
A method for making a protein or a polypeptide of interest, comprising:
- incorporating a compound into a protein or polypeptide using a selected aminoacyl-tRNA synthetase, the compound having the formula:
- or a stereoisomer or salt thereof, wherein:
- R is selected from substituted or unsubstituted C1-C6 alkyl group and substituted or unsubstituted phenyl group;
- Ra, Rb, Rc, and Rd are independently selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and halo;
- RC is hydrogen, a counter ion, or a carboxyl protecting group;
- and
- RN is hydrogen or an amine protecting group.
4 more elements
A kit, comprising:
- a tRNA;
- an aminoacyl-tRNA synthetase;
- and
- a compound having the formula:
- or a stereoisomer or salt thereof, wherein:
- R is selected from substituted or unsubstituted C1-C6 alkyl group and substituted or unsubstituted phenyl group;
- Ra, Rb, Rc, and Rd are independently selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and halo;
- RC is hydrogen, a counter ion, or a carboxyl protecting group;
- and
- RN is hydrogen or an amine protecting group,
- wherein the tRNA and aminoacyl-tRNA synthetase are an orthogonal tRNA/orthogonal aminoacyl-tRNA pair effective for incorporating the compound into a protein or polypeptide to provide a tetrazine-labeled protein.
8 more elements
Dependencies are inferred from the claim text.