HO-Ara-Glu(AEEA-AEEA-Mal)-OH

HO-Ara-Glu(AEEA-AEEA-Mal)-OH is a synthetic heterobifunctional crosslinker based on a glutamic acid scaffold. It incorporates arabinose (Ara) at the α-carboxyl position, linked via ester or amide bond, and a maleimide (Mal) group attached to the γ-carboxyl group via two AEEA (2-[2-(2-aminoethoxy)ethoxy]acetic acid) units as a flexible, hydrophilic spacer. The arabinose moiety provides a carbohydrate handle for lectin binding, while the maleimide selectively reacts with thiols in cysteine residues, enabling stable conjugation. The glutamic acid core allows further modification and serves as a central branching point, ideal for targeted drug delivery, protein modification, nanoparticle functionalization, and advanced biomaterials.

Appearance

• White to off-white solid or viscous liquid

• Likely hygroscopic

Source

• Chemically synthesized by specialized bioconjugation reagent manufacturers or custom synthesis labs

• Not commonly available from general suppliers

Molecular Weight

• Approximately 607.6 g/mol (theoretical value; may vary with counterions, protecting groups, or linkage chemistry)

Structure

• Glutamic acid core with arabinose at α-carboxyl

• γ-Carboxyl functionalized with amide-linked AEEA-AEEA chain terminated by maleimide

Biological Activity

• No intrinsic activity; function depends on conjugated molecules

• PEG-like AEEA linkers improve solubility and reduce nonspecific binding

• Arabinose may bind lectins or carbohydrate-recognizing proteins

• Glutamic acid scaffold may affect cell interactions

Purity and Microbial Contamination

Shelf Life and Storage

• Store at –20°C, dry, inert atmosphere (argon or nitrogen)

• Protect from light and moisture

• Maleimide group sensitive to hydrolysis; avoid water exposure

• Shelf life ~6–12 months

Applications

• Protein-carbohydrate conjugation via arabinose and maleimide

• Surface modification with carbohydrate handles

• Antibody-drug conjugates (ADCs) incorporating hydrophilic spacers

• Nanoparticle functionalization for targeted delivery

• Crosslinking thiol-containing entities with sugar-based ligands

Key Characteristics

• Heterobifunctional: arabinose and maleimide reactive groups

• Hydrophilic PEG-like AEEA spacer for reduced nonspecific binding

• Biocompatible design

• Maleimide selectively reacts with sulfhydryl groups

• Carbohydrate moiety enables specific molecular recognition

• Glutamic acid scaffold provides branching and modification points

• Extended flexible spacer enhances bioconjugate stability and function

Citation 

• Glutamic Acid Scaffolds: Search “Glutamic acid-based dendrimers for drug delivery”

• Maleimide Chemistry: Search “Maleimide-thiol coupling for protein conjugation”

• Carbohydrate-Protein Conjugates: Search “Carbohydrate-modified proteins for targeted drug delivery”

• AEEA Linkers: Search “AEEA linkers improve solubility and reduce aggregation” (Bioconjugate Chemistry)

• Maleimide-Thiol Drug Delivery: Search “Maleimide-thiol coupling for controlled drug release”

• Arabinose Targeting: Search “Arabinose-modified nanoparticles for targeted drug delivery”

• PEGylation for Biocompatibility: Search “PEGylation to reduce immunogenicity of proteins”

• ADC Linker Design: Search “Optimizing linker design for antibody-drug conjugates”

• Multivalent Carbohydrate Display: Search “Multivalent carbohydrate display on protein scaffolds”

• Amino Acid Linkers: Search “Amino acids as building blocks for bioconjugation”

• Flexible Spacers: Search “Flexible linkers enhance bioactivity of conjugated molecules”