Compound Modified by a Phosphoramidate And/or Phosphonamide Group and Use Thereof

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This patent discloses modified compounds—particularly biomolecules (such as proteins, peptides, or polymers)—that have been chemoselectively altered to include phosphoramidate and/or phosphonamide groups. The method allows for targeted (site-specific) modification of molecules using a variant of the Staudinger reaction, enabling the attachment of various chemical groups (e.g., PEG, biotin, fluorescent markers) without requiring toxic catalysts. These modifications are stable under mild conditions and can also be used to immobilize biomolecules on surfaces, as well as to create analogues of phosphorylated proteins.

Use CasesContent extracted from patent full text and abstract with AI.

• Site-specific labeling or modification of proteins, peptides, or polymers for biochemical research
• Development of stable, PEGylated therapeutic proteins with improved pharmacokinetic properties
• Immobilization of biomolecules on surfaces (such as nanoparticles, microplates, or quantum dots) for biosensor or high-throughput screening applications
• Preparation of phosphorylated protein analogues for studying cell signaling and enzymatic processes
• Attachment of molecular probes, fluorescent dyes, or biotin for detection and analytical purposes
• Production of kinase or phosphatase substrates and enzyme inhibitors for drug discovery and mechanistic studies

BenefitsContent extracted from patent full text and abstract with AI.

• Chemoselective, site-specific modification minimizes undesired side reactions or random modifications
• Mild reaction conditions (room temperature, aqueous buffer) preserve biomolecule function and structure
• No requirement for toxic metal catalysts (e.g., copper), allowing usage in living systems and cell-compatible environments
• Versatile compatibility with a broad range of functional groups and biomolecule types (proteins, peptides, polymers, saccharides, lipids)
• Stabilization of modified proteins (e.g., via PEGylation) enhances resistance to proteolysis and improves bioavailability
• Facilitates covalent immobilization for biosensors or screening platforms, improving reproducibility and throughput
• Allows creation of protein analogues useful for antibody generation or mechanistic signal transduction studies

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Inventors & Applicants

Patent Abstract

The invention relates to a modified compound that has at least one other functional group, in particular a biomolecule or macromolecule, characterised by at least one x-fold (x=1 ) chemoselectively incorporated phosphoramidate group of general formula (I), -NPO(OR1)(OR1'), and/or at least one x-fold (x=1 ) chemoselectively incorporated phosphonamide group of general formula (Ia), -NPO(R1XOR1'), where R1 and R1' are selected from the group containing glycerol, polyglycerol, PEG polymers of general summation formula C2nH4n+2On+1 where n = 1, Cn alkyI chains where n = 1; functionalised Cn alkyI chains where n = 1, aryls, heteroaryl, siIyI, lipids, fluorophores, saccharides, peptides, crown ethers, or a linker that links the aforementioned groups, and where R1 and R1' can be identical or different to/from one another.