Biotin-dPEG®₁₁-NH₂ (QBD-10196)

Description

Biotin-dPEG®11-NH2 (Biotin-dPEG®11-amine), product number QBD-10196, is a medium-length, hydrophilic, water-soluble, discrete PEG biotinylation product that reacts with carbonyls, carboxylic acids, and the activated esters (N-hydroxysuccinimide, 2,3,5,6-tetrafluorophenyl) of carboxylic acids. Additionally, Biotin-dPEG®11-NH2 couples directly to a carboxylic acid using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) chemistry. Furthermore, the product can react with carbonyl groups (aldehydes or ketones) to form a Schiff base, which can be reduced to a secondary amine using sodium cyanoborohydride if additional conjugate stability is necessary.

Amphiphilic biotin-dPEG®11-NH2 dissolves equally well in both aqueous buffer and organic solvent. It is not necessary to dissolve this product in an organic solvent before using it in aqueous reaction media. Furthermore, biotinylation of biomacromolecules with QBD-10196 will not cause aggregation and precipitation. Eliminating aggregation should consequently improve the signal-to-noise ratio of applications developed with this product. Reaction with a carboxylic acid or active ester of a carboxylic acid will yield a stable amide bond. Aldehydes are uncommon in biomacromolecules. However, the oxidation of reducing sugars in glycosylated proteins forms aldehydes in glycosylated proteins. Reactions with aldehydes will produce labile imines or Schiff bases that can be reduced under mild conditions with sodium cyanoborohydride to form more stable secondary amines.

Any application that can take advantage of the strong biotin-avidin/ streptavidin affinity can use Biotin-dPEG®11-NH2. The terminal amine of QBD-10196 offers the opportunity to biotinylate (1) the carbohydrate coat of glycoproteins and (2) surfaces consisting of carboxylic acids or their active esters. Thus, Biotin-dPEG®11-NH2 expands the range of molecules and nanoparticles for which dPEG®-biotin is useful.

Specifications

Documents

References

1. Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0); See pp. 529-530 for a general discussion in Greg’s book and on biotinylation as well, as well as pp. 737-738 for a protocol for a compound with just two oxygen. However, other than enhanced solubility and binding distances, the protocol is adaptable to our PN 10193.

2. Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

3. Compact Biocompatible Quantum Dots via RAFT-Mediated Synthesis of Imidazole-Based Random Copolymer Ligand. Wenhao Liu, Andrew B. Greytak, Jungmin Lee, Cliff R. Wong, Jongnam Park, Lisa F. Marshall, Wen Jiang, Peter N. Curtin, Alice Y. Ting, Daniel G. Nocera, Dai Fukumura, Rakesh K. Jain and Moungi G. Bawendi. J. Am. Chem. Soc. 2010, 132 (2) pp 472–483. December 21, 2009. DOI: 10.1021/ja908137d.