Sulfur (vi) fluoride compounds and methods for the preparation thereof
AssigneeThe Scripps Research Institute
InventorsJiajia DONG, K. Barry SHARPLESS, Jeffery W. KELLY, Aleksandra BARANCZAK, Wentao CHEN
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Abstract
This application describes modified amino acids and polypeptides comprising a SO2F or CH2CH2SO2F group bound to the side chain of an amono acid or amino acid residue of a polypeptide in place of a hydrogen of a hydroxyl or amino substituent thereof. Methods of covalently binding the polypeptides to receptot sites of receptor proteins are also described herein.
Claims20
A modified amino acid comprising an amino acid core group bound to a SO2F or CH2CH2SO2F group;
- wherein the amino acid core group has a side chain comprising a hydroxyl or amino substituent, and the SO2F or CH2CH2SO2F group is bound to the side chain in place of a hydrogen of the hydroxyl or amino substituent thereof.
A polypeptide comprising a modified amino acid residue bearing a SO2F or CH2CH2SO2F group;
- wherein the a modified amino acid residue comprises an amino acid residue core group having a side chain comprising a hydroxyl or amino substituent, and the SO2F or CH2CH2SO2F group is bound to the side chain in place of a hydrogen of the hydroxyl or amino substituent thereof.
A method for covalently attaching a SO2F or CH2CH2SO2F substituted compound to a receptor protein;
- the method comprising contacting the compound with the receptor protein in vivo;
- wherein:
- the receptor protein comprises a receptor site that includes a nucleophilic amino acid side chain in the receptor site;
- the compound is a polypeptide comprising a modified amino acid residue bearing a SO2F or CH2CH2SO2F group;
- wherein the modified amino acid residue comprises an amino acid residue core group having a side chain comprising a hydroxyl or amino substituent, and the SO2F or CH2CH2SO2F group is bound to the side chain in place of a hydrogen of the hydroxyl or amino substituent thereof,
- the compound has a molecular configuration that can interact with and dock with the receptor site;
- and
- when docked with the receptor site, the SO2F or CH2CH2SO2F group of the compound is oriented with respect to the nucleophilic side chain of the receptor site such that the nucleophilic side chain of the receptor site displaces F from the SO2F or CH2CH2SO2F group and forms a covalent bond to the S atom thereof.
Dependencies are inferred from the claim text.