Urea-Oxaziridine Library Synthesis And Applications

Patent Status

Brief Description

Chemoselective conjugation is achieved through redox reactivity by reacting a nitrogen-transfer oxidant with a thioether substrate in an aqueous environment to form a stable conjugation product. Developed by UC Berkeley researchers, this platform utilizes Redox-Activated Chemical Tagging strategies for methionine-based protein functionalization. Specifically, novel urea-oxaziridine compounds serve as oxidant-mediated reagents for direct biomolecule functionalization, converting target methionine residues into their corresponding sulfimide conjugation products. This biocompatible reaction occurs efficiently under mild, aqueous conditions, offering a powerful tool for modifying complex proteins without disrupting their native structures or biological activities.

Suggested uses

• Site-specific modification of therapeutic proteins and antibodies for targeted drug delivery applications

• Fluorescent labeling and chemical tagging of native proteins within complex biological mixtures or cellular lysates

• Development of stable bioconjugates for diagnostic assays and advanced biomaterial synthesis

• Functionalization of industrial enzymes to enhance stability, operational longevity, or substrate binding

• Structural and functional studies of oxidative stress and methionine oxidation pathways in living systems

Advantages

• Provides exceptional chemoselectivity toward methionine residues over other competing amino acids

• Operates efficiently in mild, biocompatible, and completely aqueous environmental conditions

• Eliminates the need for transition metal catalysts, reducing toxicity risks in downstream biological use

• Forms a highly stable sulfimide conjugation linkage that resists degradation during processing

• Enables direct modification of native, unengineered proteins without requiring genetic alterations

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