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04 Mar

1,2-Bis(maleimido)ethane (BMOE): A High-Performance Thiol-Bifunctional Crosslinker

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1,2-Bis(maleimido)ethane (BMOE) is a premier homobifunctional, thiol-reactive crosslinker widely utilized in structural biology, bioconjugation, and advanced polymer synthesis. With its short spacer arm and high selectivity, BMOE is a critical reagent for researchers mapping protein-protein interactions and developing stable therapeutic conjugates.

Technical Profile: BMOE (CAS 5132-30-9)

  • Chemical Name: 1,2-Bis(maleimido)ethane
  • Synonyms: BMOE, EBM, Ethylene-bis-maleimide, NSC 41127
  • Molecular Formula: C10H8N2O4
  • Molecular Weight: 220.18 g/mol
  • Spacer Arm Length: 8.0 A (Short-range)
  • Reactive Groups: Maleimide (Double-ended)

The Chemistry of BMOE: Mechanism and Selectivity

BMOE operates via the Michael Addition reaction. At physiological pH (6.5–7.5), the maleimide groups react specifically with sulfhydryl (-SH) groups to form stable thioether bonds. This reaction is significantly faster than the reaction with primary amines, making BMOE the reagent of choice for targeting cysteine residues in proteins.

Why Researchers Choose BMOE:

  1. Short-Range Crosslinking: The 8.0 Å ethylene spacer allows for "zero-length" or near-neighbor identification. If two cysteines are crosslinked by BMOE, they must be in close spatial proximity.
  2. Non-Cleavable Linkage: Unlike disulfide-based crosslinkers, the thioether bond formed by BMOE is permanent and resistant to reducing agents like DTT or TCEP.
  3. Membrane Permeability: Due to its small size and lack of charge, BMOE can often penetrate cell membranes to crosslink intracellular proteins in situ.

Critical Applications in Modern Science

1. Structural Biology and Protein Mapping

BMOE is an essential tool for determining the quaternary structure of protein complexes. By capturing transient interactions between subunits, researchers can "freeze" complexes for analysis via SDS-PAGE or Mass Spectrometry.

  • Case Study: BMOE has been used extensively to study the conformational changes in ATP-binding cassette (ABC) transporters and the assembly of viral capsids.

2. Antibody-Drug Conjugates (ADCs) & Therapeutics

In bioconjugation, BMOE serves as a linker to attach cytotoxic payloads or fluorophores to antibodies. Its stability ensures that the conjugate remains intact while circulating in the bloodstream, reducing off-target toxicity.

3. Advanced Material Science

Beyond biology, BMOE is used to create crosslinked polymer networks. It enhances the thermal stability and mechanical rigidity of resins and hydrogels, particularly those incorporating thiol-terminated polymers.

Technical Specifications & Handling

Property

Specification

Purity (HPLC)

≥ 98%

Appearance

White to Off-white powder

Solubility

Soluble in DMSO or DMF (Required prior to aqueous dilution)

Storage

Store at -20°C, desiccated to prevent hydrolysis

 

Supporting Literature & References

To ensure the highest scientific rigor, the application of BMOE is supported by the following peer-reviewed studies:

  1. Protein Proximity Mapping: Green, N. S., et al. (2001). "A Statistical Method for the Analysis of Cross-Linking Data." Bioconjugate Chemistry. (Discussing the kinetics of maleimide-thiol reactions).
  2. Cysteine-Directed Crosslinking: Smyth, D. G., et al. (1964). "Reactions of N-Ethylmaleimide with Peptides and Amino Acids." Biochemical Journal. (Foundation of maleimide selectivity).
  3. Structural Analysis: Partis, M. D., et al. (1983). "Cross-linking of proteins by omega-maleimido alkanoyl N-hydroxysuccinimide esters." Journal of Protein Chemistry.

Why Source BMOE from Finetech Industry Limited?

Finetech Industry Limited is a global leader in providing high-purity chemical reagents for the life science industry. Our 1,2-Bis(maleimido)ethane (BMOE) is manufactured under strict quality control protocols to ensure:

  • High Batch-to-Batch Consistency: Essential for reproducible research.
  • Analytical Verification: Each batch is validated via NMR and HPLC.
  • Global Logistics: Secure packaging and rapid shipping for time-sensitive projects.

For bulk inquiries, COA requests, or technical data sheets (TDS), please visit our official website or contact our technical support team.