Biotin-dPEG®₃-oxyamine. HCl

$100.00$750.00

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Biotin-dPEG®3-oxyamine·HCl, product number 11100, forms a stable oxime bond when conjugated to a ketone or aldehyde. Using this product permits biotinylation of the carbohydrate coats of glycoproteins.

Biotinylation

Biotinylation is the process of covalently attaching biotin to a molecule such as a peptide, protein, or nucleic acid, or surfaces such as glass or gold. Bioconjugation research and product development and numerous clinical assays use biotinylated molecules. The amphiphilic dPEG® linker of Biotin-dPEG®3-oxyamine·HCl imparts excellent water solubility to biotin, which is usually poorly soluble in water.

An aminooxy group (also known as an alkoxyamine) consists of a primary terminal amine adjacent to oxygen (i.e., —ONH2). This group reacts selectively and efficiently with aldehydes to form an aldoxime linkage and with ketones to form a ketoxime linkage. An oxime bond is more stable than a hydrazone bond and does not need to be reduced to a secondary amine to stabilize it.

Aldehydes and ketones occur relatively rarely in nature; however, using sodium periodate, aldehydes can be formed in glycoproteins whose carbohydrate coats contain reducing sugars. Moreover, scientific literature examples demonstrate the introduction of ketones into bacterial cell walls through liposomal fusion1,2.

Some commercially available biotin-aminooxy products use either no spacer or a hydrophobic, alkyl chain as a spacer between biotin and the aminooxy moiety. Such products have poor solubility in water and must be dissolved in a dry organic solvent such as dimethyl sulfoxide (DMSO) immediately before use, which can be problematic under some conditions. If used on proteins, these hydrophobic products may trigger aggregation and precipitation of the biotinylated molecule. Even if aggregation and precipitation do not occur, the hydrophobic spacer can contribute to non-specific binding. Because it is amphiphilic, Biotin-dPEG®3-oxyamine·HCl can be dissolved in water or aqueous buffer and used directly in a conjugation reaction. PN11100 will not cause aggregation or precipitation of the biotinylated molecule. Moreover, the hydrophilicity of the dPEG® linker reduces or eliminates non-specific binding.

At Quanta BioDesign, Ltd., we sell Biotin-dPEG®3-oxyamine·HCl as the hydrochloride salt. A longer version of this product, PN11102, Biotin-dPEG®11-oxyamine·HCl, is also available.

If you need bulk product in a larger package size than our standard sizes, please contact us for a quote. Our commercial capabilities permit us to manufacture this product at any scale that you need.

Learn more!

What is dPEG®?

Frequently Asked Questions (about dPEG® products)

Biotinylation with dPEG® products

Application References:

  1. Elahipanah, S.; Radmanesh, P.; Luo, W.; O’Brien, P. J.; Rogozhnikov, D.; Yousaf, M. N. Rewiring Gram-Negative Bacteria Cell Surfaces with Bio-Orthogonal Chemistry via Liposome Fusion. Bioconjugate Chem. 2016, 27(4), 1082–1089. https://doi.org/10.1021/acs.bioconjchem.6b00073.
  2. Elahipanah, S. Development of a New General Click Chemistry and Applications in Bioconjugation: Part I: Rewiring Bacteria Cell Surfaces with Bio-Orthogonal Chemistry Part II: A Novel General Dialdehyde Click Chemistry for Primary Amine Conjugation. 2017. Ph.D. Dissertation, York University, Toronto, Ontario, Canada. https://yorkspace.library.yorku.ca/xmlui/handle/10315/34274

Additional information

Weight.5 oz
Dimensions.75 × .75 × 2 in