Biotin-dPEG®₁₁-oxyamine. HCl

Biotin-dPEG®11-oxyamine·HCl, product number 11102, is a biotinylation reagent from Quanta BioDesign that forms a stable oxime bond when conjugated to a ketone or aldehyde. The use of Biotin-dPEG®11-oxyamine·HCl permits the biotinylation of the carbohydrate coats of glycoproteins.

Biotinylation is the process of covalently attaching biotin to biomolecules or surfaces such as glass and gold. Biotin finds extensive use in bioconjugation research and product development and medical diagnostics. Although biotin is poorly water-soluble, the amphiphilic dPEG® linker imparts excellent solubility in aqueous media and organic solvents.

Traditional biotinylation reagents either modify biotin directly or couple biotin to aminocaproic acid (abbreviated LC, for "long chain") and then add the appropriate reactive group. LC-biotin constructs are hydrophobic. Therefore, dissolution in an organic solvent (typically DMSO) is required to use them. Their hydrophobic nature can trigger rapid aggregation of biotinylated molecules.

Aldehydes and ketones occur relatively rarely in nature. However, sodium periodate forms aldehydes in glycoproteins whose carbohydrate coats contain reducing sugars. Moreover, literature examples demonstrate the introduction of ketones into bacterial cell walls through liposomal fusion1,2.

Biotin-LC-hydrazide is frequently used to modify glycoproteins' carbohydrate coats. The hydrazone linkage formed is unstable at low pH. Thus, reduction of the hydrazone to a second amine is necessary for stability. The LC linker's hydrophobicity requires caution to avoid over conjugating the target molecules. Moreover, even if aggregation and precipitation do not occur, the hydrophobic spacer can contribute to non-specific binding.

Aminooxy groups consist of a primary terminal amine next to oxygen (—ONH2). This group reacts with aldehydes to form aldoxime bonds and with ketones to form ketoximes. An oxime bond is more stable than a hydrazone bond. Stabilization of the oxime bond through reduction to a secondary amine is unnecessary.
Using Biotin-dPEG®11-oxyamine·HCl
Because it is amphiphilic, Biotin-dPEG®11-oxyamine·HCl can be dissolved in water or aqueous buffer and used directly in a conjugation reaction. PN11102 will not cause aggregation or precipitation of the biotinylated molecule. Moreover, the hydrophilicity of the dPEG® linker reduces or eliminates non-specific binding.

Biotin-dPEG®3-oxyamine·HCl is sold as the hydrochloride salt. A shorter version of this product, PN11100, Biotin-dPEG®3-oxyamine·HCl, is also available.

Application References:
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.
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
Hermanson, G. T. Chapter 11, (Strept)avidin-Biotin Systems. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, 465-505.
Hermanson, G. T. Chapter 18, PEGylation and Synthetic Polymer Modification. Bioconjugate Techniques, 3rd edition. Academic Press: New York, 2013, 787-838.

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