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US 10,577,391 B2Granted
Selective photoactivation of amino acids for single step peptide coupling
AssigneeVibrant Holdings, LLC
InventorVasanth Jayaraman
Life of this patent
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Abstract
Disclosed herein are formulations, substrates, and arrays for amino acid and peptide synthesis on microarrays. In certain embodiments, methods for manufacturing and using the formulations, substrates, and arrays including one-step coupling, e.g., for synthesis of peptides in a C→N orientation are disclosed. In some embodiments, disclosed herein are formulations and methods for high efficiency coupling of biomolecules to a substrate.
Claims14
A method of attaching a coupling molecule to a substrate, comprising:
- obtaining a substrate comprising a plurality of amine groups for linking to a coupling molecule;
- contacting said substrate with a carboxylic acid activating formulation comprising:
- a carboxylic acid activating compound, wherein said compound is 1-(3-(diethylamino)-propyl)-4-(2-methoxyphenyl)-1,4-dihydro-5H-tetrazole-5-thione, a coupling molecule, and a solvent;
- selectively exposing said photoactive coupling formulation to light, thereby activating a carboxylic group of said coupling molecule at a selectively exposed area;
- coupling the activated carboxylic group of said coupling molecule to at least one of said plurality of amine groups at said selectively exposed area, wherein said coupling is performed multiple times at different selectively exposed areas on said substrate and wherein said coupling step has a coupling efficiency of at least 98.5%;
- and
- optionally repeating said method to produce a desired polymer at said at least one carboxylic acid group.
4 more elements
A method of attaching a coupling molecule to a substrate, comprising:
- obtaining a substrate comprising a plurality of amine groups for linking to a coupling molecule;
- contacting said substrate with a carboxylic acid activating formulation comprising:
- a carboxylic acid activating compound, wherein said compound is 1-(3-(diethylamino)-propyl)-4-(2-methoxyphenyl)-1,4-dihydro-5H-tetrazole-5-thione, a coupling molecule, and a solvent;
- selectively exposing said photoactive coupling formulation to light, thereby activating a carboxylic group of said coupling molecule at a selectively exposed area;
- coupling the activated carboxylic group of said coupling molecule to at least one of said plurality of amine groups at said selectively exposed area, wherein said coupling is performed multiple times at different selectively exposed areas on said substrate and wherein said coupling step has a coupling efficiency of at least 90%;
- and
- optionally repeating said method to produce a desired polymer at said at least one carboxylic acid group.
4 more elements
A method of attaching a coupling molecule to a substrate, comprising:
- obtaining a substrate comprising a plurality of amine groups for linking to a coupling molecule;
- contacting said substrate with a carboxylic acid activating formulation comprising:
- a carboxylic acid activating compound, wherein said compound is 1-(3-(diethylamino)-propyl)-4-(2-methoxyphenyl)-1,4-dihydro-5H-tetrazole-5-thione, a coupling molecule comprising an amino acid with an Fmoc protecting group attached to an amine group, and a solvent;
- selectively exposing said photoactive coupling formulation to light, thereby activating a carboxylic group of said coupling molecule at a selectively exposed area;
- coupling the activated carboxylic group of said coupling molecule to at least one of said plurality of amine groups at said selectively exposed area;
- and
- optionally repeating said method to produce a desired polymer at said at least one carboxylic acid group.
4 more elements
A method of attaching a coupling molecule to a substrate, comprising:
- obtaining a substrate comprising a plurality of amine groups for linking to a coupling molecule;
- contacting said substrate with a carboxylic acid activating formulation comprising:
- a carboxylic acid activating compound, wherein said compound is 1-(3-(diethylamino)-propyl)-4-(2-methoxyphenyl)-1,4-dihydro-5H-tetrazole-5-thione, a coupling molecule comprising an amino acid with an Fmoc protecting group attached to an amine group, and a solvent;
- selectively exposing said photoactive coupling formulation to light, thereby activating a carboxylic group of said coupling molecule at a selectively exposed area;
- coupling the activated carboxylic group of said coupling molecule to at least one of said plurality of amine groups at said selectively exposed area, wherein said coupling is performed multiple times at different selectively exposed areas on said substrate and wherein said coupling step has a coupling efficiency of at least 90%;
- and
- optionally repeating said method to produce a desired polymer at said at least one carboxylic acid group.
4 more elements
A method of attaching a coupling molecule to a substrate, comprising:
- obtaining a substrate comprising a plurality of amine groups for linking to a coupling molecule;
- contacting said substrate with a carboxylic acid activating formulation comprising:
- a carboxylic acid activating compound, wherein said compound is 1-(3-(diethylamino)-propyl)-4-(2-methoxyphenyl)-1,4-dihydro-5H-tetrazole-5-thione, a coupling molecule comprising an amino acid with an Fmoc protecting group attached to an amine group, and a solvent;
- selectively exposing said photoactive coupling formulation to light, thereby activating a carboxylic group of said coupling molecule at a selectively exposed area;
- coupling the activated carboxylic group of said coupling molecule to at least one of said plurality of amine groups at said selectively exposed area, wherein said coupling is performed multiple times at different selectively exposed areas on said substrate and wherein said coupling step has a coupling efficiency of at least 98.5%;
- and
- optionally repeating said method to produce a desired polymer at said at least one carboxylic acid group.
4 more elements
Dependencies are inferred from the claim text.