This product is a high-performance, dual-functional heterobifunctional PEG (polyethylene glycol) crosslinking reagent. One end of the molecule features a protected primary amino group, while the other end contains an activated succinimidyl ester, connected by a customizable PEG spacer. This unique design makes it an indispensable "bridge" molecule in bioconjugation, material modification, and drug development, particularly in PROTAC technology.
II. Structural Features and Advantages
t-Boc-protected amino end: Chemically stable, can be selectively deprotected under acidic conditions (e.g., TFA or HCl in organic solvents) to release a reactive primary amine (-NH₂). This free amine can react with isocyanates, activated carboxylic acids, acyl chlorides, and other functional groups.
NHS ester end: Under mild pH 7–9 buffer conditions, it efficiently and specifically reacts with primary amines (-NH₂) on biomolecules (e.g., proteins, peptides, antibodies) or material surfaces via amidation, forming stable covalent bonds.
Tunable PEG spacer: PEG chain length can be precisely selected, allowing fine control over water solubility, steric hindrance, and linker length.
Short-chain PEG (n = 1–4): Provides rigidity and short-distance connection, reduces conformational freedom, ideal for applications requiring precise positioning or rigid linkages.
Medium/long-chain PEG (n = 5–12): Significantly enhances water solubility, offers longer and more flexible linkers, helps overcome steric hindrance, and improves biomolecular recognition and binding efficiency.
Excellent physicochemical properties:
Incorporation of PEG chains improves biocompatibility, reduces immunogenicity, and prolongs in vivo circulation half-life.
Defined molecular structure and weight enable easy mass spectrometry characterization and precise reaction stoichiometry control.
III. Key Applications
PROTAC (Proteolysis-Targeting Chimera) Development:
Key linker component: t-Boc-NH-PEGn-NHS is an ideal building block for constructing PROTAC molecules.
Conjugation strategy: The NHS end first reacts with an E3 ligase ligand (e.g., lenalidomide-, VHL-, or CRBN-based ligands) or a target protein ligand containing a primary amine. After deprotection of the t-Boc group, the exposed primary amine is used to attach the other ligand (e.g., via amidation, ureidation), enabling efficient synthesis of PROTAC libraries with varied linker lengths and flexibilities.
Functional optimization: By screening different PEG chain lengths (n = 1–12), researchers can systematically study the impact of linker length and properties on PROTAC ternary complex formation, cell permeability, degradation activity, and selectivity — a core tool for optimizing degrader efficacy.
Bioconjugation and Labeling:
In ADC (antibody-drug conjugate) or fluorescent probe synthesis, serves as a linker for site-specific conjugation of drugs or reporter groups (e.g., fluorescein, biotin) to antibodies or proteins.
Used for immobilizing peptides, proteins, or other biomolecules onto amine-functionalized material surfaces (e.g., chips, microspheres, nanoparticles).
Functional Material Synthesis:
Acts as a macromonomer or crosslinker for synthesizing smart hydrogels, polymer brushes, and coatings with stimuli-responsive (post t-Boc deprotection generates amines) or bioactive sites.
Modifies nanoparticle surfaces to introduce protected amino groups for subsequent functionalization.
Organic Synthesis and Medicinal Chemistry:
Serves as a protecting group/linker in peptide synthesis or small-molecule drug modification to introduce hydrophilic PEG segments, improving drug solubility and pharmacokinetic properties.
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