Biocytin hydrazide 

Biocytin hydrazide is a long-chain biotin-containing hydrazide, serving as a biotin-derived active coupling reagent, selective labeling agent and biotinylating reagent. Biocytin hydrazide targets aldehyde, carboxyl, amino and guanidino groups to biotinylate glycoconjugates, K99 lectin, peptides and proteins through its hydrazide moiety, and achieves nonradioactive detection of sialic acid- and galactose-containing glycoconjugates via the avidin–biotin system^[1][2][3].

Biocytin hydrazide (0.3-30 μg/mL) optimally labels oxidized fetuin and asialofetuin on dot blots at a concentration of 3 μg/mL^[1].
Biocytin hydrazide (3 μg/mL; 1 h, 2 h) labels human erythrocyte membrane glycoproteins on blots via both periodate oxidation (3 μg/mL, 1 h) and NAGO oxidation (3 μg/mL, 2 h), producing similar banding patterns with NAGO requiring higher protein input^[1].
Biocytin hydrazide (10-100 μg/mL; 1 h, 2 h) labels human erythrocyte membrane glycoproteins via periodate oxidation (10-100 μg/mL, 1 h), NAGO oxidation (10-100 μg/mL, 2 h), or GO oxidation (10-100 μg/mL, 2 h); GO treatment selectively labels the Band 3 glycoprotein, while periodate treatment alters membrane protein electrophoretic mobility^[1].
Biocytin hydrazide achieves site-specific biotinylation of K99 lectin via carboxyl groups. The obtained biotinylated K99 lectin can specifically bind to sialic acid-containing receptors on HeLa cells and recapitulate the adhesion pattern of intact K99-expressing E. coli B80. Meanwhile, biotinylated K99 lectin retains specific recognition capacity toward NeuGc-GM3 ganglioside with a detection limit of 90 ng, showing equivalent sensitivity to intact K99-expressing bacteria^[2].
Biocytin hydrazide (0.01-1 M; 5-96 h) directly biotinylates peptides including human angiotensin I, P₁₄R, ACTH fragment 1-13, and proteins including bovine insulin, horse heart cytochrome c, hen egg white lysozyme, soybean trypsin inhibitor, and bovine serum albumin via its hydrazide moiety, binding to arginine side chains along with other residues, with efficiency increasing with higher temperature, higher concentration, and longer incubation time, and optimal activity at neutral pH^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

386.51

C₁₆H₃₀N₆O₃S

102743-85-1

Solid

White to light yellow

NNC([C@@H](N)CCCCNC(CCCC[C@H]1[C@]2([H])[C@](NC(N2)=O)([H])CS1)=O)=O

Room temperature in continental US; may vary elsewhere.

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

• [1]. Bayer EA, et al. Biocytin hydrazide--a selective label for sialic acids, galactose, and other sugars in glycoconjugates using avidin-biotin technology. Anal Biochem. 1988;170(2):271-281.  [Content Brief]

  [2]. Ouadia A, et al. Detection of the ganglioside N-glycolyl-neuraminyl-lactosyl-ceramide by biotinylated Escherichia coli K99 lectin. Glycoconj J. 1992;9(1):21-26.  [Content Brief]

  [3]. Lee BS. Biotinylation of Peptides/Proteins Using Biocytin Hydrazide. J Chin Chem Soc. 2007;54(2):541-548.