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EZ-Link BMCC-Biotin


A cysteine-biotinylation reagent with an extended cyclohexane spacer arm.

EZ-Link BMCC-Biotin

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:

Chemical structure of BMCC-Biotin
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:

  1. 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.
  2. Cadieux. N., et al. (2003). Differential substrate-induced signaling through the TonB-dependent transporter BtuB. Proc. Natl. Acad. Sci. USA 100:10688.
  3. 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.
  4. 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.
  5. Finkelstein, E.I., et al. (2005). Regulation of constitutive neutrophil apoptosis by the α,β-unsaturated aldehydes acrolein and 4-hydroxynonenal. Am. J. Physiol. Lung. Cell. Mol. Physiol. 289:L1019-28.
  6. 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.
  7. Luo, B-H., et al. (2004). Locking the β3 integrin I-like domain into high and low affinity conformations with disulfides. J. Biol. Chem. 279:10215-21.
  8. Politis, E.G., et al. (2005). Transmembrane topology of the protein palmitoyl transferase Akr1. J. Biol. Chem. 280: 10156-63.
  9. 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


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
21900 EZ-Link BMCC-Biotin
Formulation: Maleimide-activated biotin with an amido-(cyclohexane-carboxamide)butane spacer
Sufficient For: Approx. 25 uses to label a total of 625mg of IgG using typical conditions
50mg Product Instructions for product #21900 EZ-Link BMCC-Biotin MSDS for product #21900 EZ-Link BMCC-Biotin Certificate of Analysis for product #21900 EZ-Link BMCC-Biotin $208.00

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Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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