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US 12,686,701 B2Granted
Substitution of histidine with 2-thiohistidine in bioactive peptides
AssigneeUniversity of Vermont and State Agricultural College
InventorsRobert J. Hondal, Kaelyn Jenny
Life of this patent
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Abstract
Presented is a method to incorporate 2-thiohistidine (2-thioHis) into a peptide. Also provided are peptides incorporating 2-thioHis, compositions, and methods of using the peptides incorporating 2-thioHis. The methods may be methods for scavenging metals and/or radicals or reducing oxidative stress. 2-thioHis has the following structure
Claims18
A method for making a modified peptide comprising:
- contacting a reaction mixture comprising a solvent,
- optionally, a carbodiimide, and, optionally, a base,
- wherein R is an amine protecting group and R′ is an H or group formed from a carbodiimide, with:
- i) an amine group of a first amino acid covalently attached to a resin, peptide covalently attached to a resin, a peptidomimetic covalently attached to a resin, or resin, or
- ii) an alcohol of a first amino acid derivative attached to a resin, peptidomimetic attached to a resin, or resin, or
- iii) a carbocation of a resin;
- optionally, removing the amine protecting group of the amine group of
- optionally, coupling a second amino acid, wherein the second amino acid is N-protected, to the unprotected amine;
- optionally, cleaving the N-protecting group of the second amino acid,
- optionally, repeating the coupling amino acid step and subsequent cleaving N-protecting group step;
- and
- cleaving the modified peptide from the resin,
- wherein the modified peptide is formed.
10 more elements
A modified peptide comprising:
- (SEQ ID NO:1, where His is replaced with 2-thioHis),
- wherein is a R″ is H, a capping group, a linking group, a peptide group, or a linking group covalently bonded to a capping group and R′″ is —OH, —NH2, —OR″″, where R″″ is an alkyl group.
Dependencies are inferred from the claim text.