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EZ-Link Hydrazide-Biocytin


A mid-length biotinylation reagent for labeling aldehyde groups.

EZ-Link Hydrazide-Biocytin

Thermo Scientific EZ-Link Hydrazide-Biocytin is a mid-length, hydrazide-activated biotinylation reagent that contains an extra amine for greater reagent solubility during labeling reactions with carbonyl-containing compounds.

Hydrazide-activated biocytin enables simple and efficient biotin labeling of polyclonal antibodies and other glycoproteins. Mild oxidation of sialic acid sugars with sodium periodate produces reactive aldehydes that can be conjugated to hydrazides. This compound is identical to Biotin-LC-Hydrazide (Part No. 21340), except that it possesses an additional primary amine in its spacer arm. This makes the reagent slightly more soluble and also makes possible other labeling and conjugation applications.

Highlights:

  • Glycoprotein labeling – biotinylate glycosylated proteins at sialic acid residues for detection or purification using streptavidin probes or resins
  • Cell surface labeling – biotinylate and isolate cell surface glycoproteins; reagent does not permeate membranes of whole cells
  • Aldehyde-reactive – reacts with aldehydes formed by periodate-oxidation of sugar groups
  • Hydrazide-activated – perform reactions at pH 4 to 6 in buffers such as sodium acetate
  • Irreversible – forms semi-permanent hydrazone bonds; spacer arm cannot be cleaved
  • Solubility – usually dissolved in DMSO before further dilution in aqueous buffers
  • Medium length – spacer arm (total length added to target) is 19.7 angstroms; contains an additional primary amine, which can be targeted as a second conjugation point

Product Details:

Chemical structure of Hydrazide-Biocytin
Chemical structure of Hydrazide-Biocytin. This biotinylation reagent labels glycoproteins and other molecules having carbohydrates that can be oxidized with periodate to expose aldehydes. For more information, see our review of Hydrazide Reaction Chemistry.

Properties of Hydrazide-Biocytin. This aldehyde-reactive biotinylation reagent has an intermediate-length spacer arm, which contains an additional primary amine.
Alternative names Biocytin-hydrazide; Hydrazide-activated biocytin
Chemical name 2-amino-6-(biotinamido)hexanehydrazide
SMILES structure O=C(CCCCC(SC1)C2C1NC(N2)=O)NCCCCC(N)C(NN)=O
Molecular formula C16H30N6O3S
Molecular weight 386.51
Spacer arm length 19.7 angstroms
Mass added to target 368.20 daltons
Form White powder
Solubility Approx. 5mM in water; approx. 50mM in DMSO; poorly soluble in DMF
Storage conditions Room temperature
Reactive groups Hydrazide, reacts with aldehydes at pH 4 to 6

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. Hydrazides and alkoxyamines are two types of carbonyl-reactive groups. Hydrazides (–NH-NH2) react specifically with aldehyde groups in slightly acidic conditions to form hydrazone linkages; these can be further reduced to stable secondary amine bonds using sodium cyanoborohydride (Part No. 44892). The reaction is more efficient in the presence of aniline (Part No. 88944). Alternatively, hydrazides can be conjugated to carboxylic acids using EDC carbodiimide chemistry.

Reactive aldehyde groups can be generated in glycoproteins and other polysaccharide compounds by oxidation of constituent sugar diols using sodium periodiate (Part No. 20504). Sialic acid residues are common components of protein glycosylation and are easily converted to aldehydes with 1mM NaIO4.

Applications:

  • Labeling erythrocyte membranes (Ref.1)
  • Labeling cytosine residues in DNA and RNA via a bisulfite-catalyzed transamination reaction (Ref.2)
  • Labeling of resolved glycoproteins on blots using either a galactose oxidase or a periodate oxidation method (Ref.3)

References:

  1. Roffman, E., Meromsky, L., Ben-Hur, H., Bayer, E.A. and Wilchek, M. (1986). Biochem. Biophys. Res. Comm. 136, 80-85.
  2. Reisfield, A., Rosenberg, J.M., Bayer, E.A. and Wilchek, M. (1987). Biochem. Biophys. Res. Comm. 142, 519-526.
  3. Bayer, E.A., Ben-Hur, H. and Wilchek, M. (1988). Anal. Biochem. 170, 271-281.

Related Resources:

Biotinylation Reagents Selection Guide
Review of Biotinylation Methods and Applications
Review of Glycosylation and Glycoprotein Methods
Chemistry of Crosslinking (and Labeling Reagents)

Related Products:

Hydrazide-PEG4-Biotin – long, hydrophilic, PEGylated spacer arm
Sodium meta-Periodate – carbohydrate oxidation reagent
All Biotinylation Reagents
Avidin, Streptavidin, NeutrAvidin Affinity Resins


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
28020 EZ-Link Hydrazide-Biocytin
Formulation: Hydrazide-activated biotin with an L-lysine spacer
Sufficient For: Approx. 12 uses to label a total of 13mg of IgG (oxidized glycoprotein) using typical conditions
25mg Product Instructions for product #28020 EZ-Link Hydrazide-Biocytin MSDS for product #28020 EZ-Link Hydrazide-Biocytin Certificate of Analysis for product #28020 EZ-Link Hydrazide-Biocytin $209.00

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Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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