Thermo Scientific EZ-Link BMCC-Biotin is a maleimide-activated, sulfhydryl-reactive biotinylation reagent with an extended spacer arm that contains a stabilizing cyclohexane group.
BMCC-Biotin is a maleimido-biotin compound for labeling protein cysteines and other molecules that contain sulfhydryl groups. This reagent specifically reacts with reduced thiols (-SH) in near-neutral buffers to form permanent (irreversible) thioether bonds. The unique feature of BMCC-Biotin is its spacer arm cyclohexane ring; this has a stabilizing effect that minimizes hydrolysis and degradation of the maleimide group until it has opportunity to conjugate with target thiols.
Highlights:
- Protein labeling – biotinylate antibodies or other proteins for use in protein methods
- Membrane-permeable – can be used to label inside cells (intracellular)
- Thiol-reactive – reacts with sulfhydryls (-SH), such as the side-chain of cysteine (C)
- Maleimide-activated – perform reactions at pH 6.5 to 7.5 in buffers such as PBS
- Irreversible – forms permanent thioether bonds; spacer arm cannot be cleaved
- Solubility – must be dissolved in DMSO or DMF before further dilution in aqueous buffers
- Medium length – spacer arm (total length added to target) is 32.6 angstroms; contains cyclohexane ring, which stabilizes adjacent maleimide
Product Details:
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| Chemical structure of BMCC-Biotin. This biotinylation reagent labels antibodies and other proteins and molecules that contain sulfhydryl groups (e.g., side-chain of cysteine). For more information, see our review of Maleimide Reaction Chemistry. |
| Properties of BMCC-Biotin. This sulfhydryl-reactive compound has an extended spacer arm, which contains a cyclohexane ring that stabilizes the maleimide group. |
| Alternative names |
Biotin-BMCC |
| Chemical name |
1-Biotinamido-4-[4'-(maleimidomethyl)cyclohexanecarboxamido]butane |
| SMILES structure |
O=C(CCCCC(SC1)C2C1NC(N2)=O)NCCCCNC(C3CCC(CN4C(C=CC4=O)=O)CC3)=O |
| Molecular formula |
C26H39N5O5S |
| Molecular weight |
533.68 |
| Spacer arm length |
32.6 angstroms |
| Mass added to target |
533.27 daltons |
| Form |
White to off-white powder |
| Storage conditions |
4°C with desiccant, protect from moisture |
| Reactive groups |
Maleimide, reacts with sulfhydryls at pH 6.5-7.5 |
We manufacture biotin reagents to ensure the highest possible overall product integrity, consistency and performance for the intended research applications.
Biotinylation reagents differ in reactivity, length, solubility, cell permeability and cleavability. Three types of sulfhydryl-reactive compounds are available: maleimido, iodoacetyl and pyridyldithiol. Maleimide reagents specifically react with sulfhydryl groups (-SH) in near-neutral buffers to form permanent thioether bonds.
In proteins, sulfhydryls exist where there are cysteine (C) residues. Cystine disulfide bonds must be reduced to make sulfhydryl groups available for labeling. Hinge-region disulfide bridges of antibodies can be selectively reduced to make functional half-antibodies that can be labeled.
References:
- Atanasijevic, T., et al. (2006). Calcium-sensitive MRI contrast agents based on superparamagnetic iron oxide nanoparticles and calmodulin. Proc. Natl. Acad. Sci. USA 103:14707-12.
- Cadieux. N., et al. (2003). Differential substrate-induced signaling through the TonB-dependent transporter BtuB. Proc. Natl. Acad. Sci. USA 100:10688.
- Chenette, E.J., et al. (2006). Multiple sequence elements facilitate Chp rho GTPase subcellular location, membrane association, and transforming activity. Mol. Biol. Cell. 17:3108-21.
- Ching, K.H., et al. (2005). The role of SPECs, small Cdc42-binding proteins, in F-actin accumulation at the immunological synapse. J. Biol. Chem. 280:23660-7.
- Finkelstein, E.I., et al. (2005). Regulation of constitutive neutrophil apoptosis by the a,b-unsaturated aldehydes acrolein and 4-hydroxynonenal. Am. J. Physiol. Lung. Cell. Mol. Physiol. 289:L1019-28.
- Hou, H., et al. (2005). The DHHC protein Pfa3 affects vacuole-associated palmitoylation of the fusion factor Vac8. Proc. Natl. Acad. Sci. USA 102:17366-71.
- Luo, B-H., et al. (2004). Locking the b3 integrin I-like domain into high and low affinity conformations with disulfides. J. Biol. Chem. 279:10215-21.
- Politis, E.G., et al. (2005). Transmembrane topology of the protein palmitoyl transferase Akr1. J. Biol. Chem. 280: 10156-63.
- Wan, Y., et al. (2004). Increased site 1 affinity improves biopotency of porcine growth hormone: evidence against diffusion dependent receptor dimerization. J. Biol. Chem. 279:44775-84.
Related Resources:
Biotinylation Reagents Selection Guide
Review of Biotinylation Methods and Applications
Chemistry of Crosslinking (and Labeling Reagents)
Related Products:
All Biotinylation Reagents
Biotin Quantitation Reagents and Kits
Avidin, Streptavidin, NeutrAvidin Affinity Resins
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