Redox-based reagents for methionine bioconjugation
AssigneeThe Regents of the University of California
InventorsShiXian Lin, XiaoYu Yang, F. Dean Toste, Christopher J. Chang
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Abstract
Chemoselective conjugation is achieved through redox reactivity by reacting an N-transfer oxidant with a thioether substrate in a redox reaction in an aqueous environment to form a conjugation product. In embodiments, Redox-Activated Chemical Tagging (ReACT) strategies for methionine-based protein functionalization. Oxaziridine (Ox) compounds serve as oxidant-mediated reagents for direct functionalization by converting methionine to the corresponding sulfimide conjugation product.
Claims10
A redox-activated chemical tagging (ReACT) method for functionalization of a protein having a surface accessible methionine residue, the method comprising contacting the protein in a non-denatured state with a urea oxaziridine in a buffered aqueous environment under conditions wherein the protein remains non-denatured and the urea oxaziridine directly functionalizes the protein by converting the surface-accessible methionine residue of the protein to the corresponding sulfimide conjugation product, without converting any surface inaccessible methionine residues of the protein, wherein the urea oxaziridine has the structure:
- wherein:
- R1 is —C(O)NHR8, and R8 is C1-6 alkyl optionally substituted with C2-6 alkynyl, C2-6 alkynyloxy, or —N3;
- R2 is H, C1-6 alkyl, or C1-6 haloalkyl;
- and
- R3 is phenyl.
Dependencies are inferred from the claim text.