3-Maleimidopropionic Acid: Versatile Reagent for Precise Bioconjugation
3-Maleimidopropionic Acid (3-MPA), also known as Mal-(CH₂)₂-COOH, with CAS number 7423-55-4, is a crucial chemical reagent in the field of bioconjugation. It features a maleimide group and a terminal carboxylic acid, offering exceptional versatility for various applications.
Chemical Structure and Functional Groups
- Maleimide Group (-NHCOCH=CH₂): This reactive group forms stable covalent bonds with thiol groups, creating robust thioether linkages. It is essential for conjugating with thiol-containing molecules like cysteine residues in proteins and peptides.
- Terminal Carboxylic Acid Group (-CH₂-CH₂-COOH): The carboxylic acid at the end of the PEG chain readily reacts with primary and secondary amines. This reaction occurs under conditions such as EDC, DCC, HATU, or other amide coupling methods to form stable amide bonds, allowing for further functionalization or conjugation.
Applications of 3-Maleimidopropionic Acid
- Antibody-Drug Conjugates (ADCs):
- Pharmaceutical Development: 3-MPA is used to link cytotoxic drugs to antibodies, creating ADCs. The maleimide group ensures specific attachment to thiol groups on antibodies, while the carboxylic acid group allows for additional modifications or conjugations.
- Protein and Peptide Labeling:
- Bioconjugation: The maleimide functionality reacts with thiol groups on proteins or peptides, enabling precise labeling or modification. This is essential for studying proteins in various assays.
- Diagnostic Assays:
- Biomarker Detection: In diagnostic assays, 3-MPA facilitates the creation of stable conjugates between biomarkers and detection agents, with the maleimide group providing reliable bonding and the carboxylic acid group enabling further functionalization.
- Drug Delivery Systems:
- Targeted Therapies: 3-MPA aids in developing targeted drug delivery systems by conjugating drugs to targeting molecules or carriers, optimizing therapeutic delivery.
Benefits of 3-Maleimidopropionic Acid
- Stable Conjugation: The maleimide group forms strong covalent bonds with thiol groups, ensuring stable and reproducible conjugation.
- Versatile Reactivity: The carboxylic acid group allows reactions with primary and secondary amines under various coupling conditions, enhancing the reagent’s flexibility.
- Customizable: Enables further modifications for diverse applications in bioconjugation.
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