1,2-Bis(maleimido)ethane (BMOE): A High-Performance Thiol-Bifunctional Crosslinker
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:
- 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.
- Non-Cleavable
Linkage: Unlike disulfide-based
crosslinkers, the thioether bond formed by BMOE is permanent and resistant
to reducing agents like DTT or TCEP.
- 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:
- 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).
- Cysteine-Directed
Crosslinking: Smyth, D.
G., et al. (1964). "Reactions of N-Ethylmaleimide with Peptides
and Amino Acids." Biochemical Journal. (Foundation of
maleimide selectivity).
- 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.