Biotin-dPEG®x-NH2

Amount: 100mg

Item Name: Biotin-dPEG®11-NH2

Item #: 10196

Mol. Wt.: 770.97;

single compound dPEG® Spacer is 37 atoms and 44.1 A

Product Features and Benefits: A Carbonyl reactive dPEG® pegylation biotinylation reagent, making the labeled product very hydrophilic and the biotin very available for streptavidin binding in the capture/binding step. With conventional reagents with the LC linker the biotin may lay on the surface of the labeled material and not be as available for binding streptavidin! Spacer is approximately the same length as 10200 (dPEG®4 with NHS ester), and its length is optimal for rapid and tight avidin/SA binding properties. Reference and

Protocol: Greg T. Hermanson, Bioconjugate Techniques, 2nd Ed, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). See pages 529 and 530 for a general discussion in Greg’s book and on biotinylation as well, as well as pp. 737 and 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.

Amount: 100mg

Item Name: Biotin-dPEG®7-NH2

Item #: 10826

Mol. Wt.: 594.76;

single compound dPEG® Spacer is 25 atoms and 29.8 A

Product Features and Benefits: Completely unique dPEG®- containing biotinylation pegylation reagent containing terminal azide functionality, which can be used as a protected amine, or available as a partner in either a click or Staudinger coupling application. The azide can be reacted with an acetylene moiety (Click reaction) or an arylphospine as part of several Staudinger ligation options (see references) dPEG® spacer is extremely hydrophilic and non-immunogenic/ non-antigenic dPEG3+4® is a 31 atom, 36 Angstrom long conjugate spacer Spacer will reduce or eliminate problems with aggregation and immunogenicity -- typically issues with conventional crosslinkers Applications: Two very active areas of development using the azide functionality are a) “Click” chemistry, the particular example of the CuI catalyzed reaction of the azide and a terminal acetylene; and b) the Staudinger ligation using functionalize daryl phosphines to couple the azide in a covalent fashion to form amides. The tremendous attraction to the azide functionality is its very low reactivity and high stability under most conditions, especially where other conjugating functionality have to be used very cautiously due to their limited stability, or require careful control of variables like pH in order to insure high yielding reactions. However, under very specific conditions, the azide is very reactive and highly selective in its reactivity. As is the case in the current very economically competitive environment, many of the applications of these chemistries may be protected intellectual property. Protocols: For particular protocols, please look in the references cited or more detailed application references contained within.

References: General: See Greg T. Hermanson, Bioconjugate Techniques, 2nd Ed, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0), and specifically see pp. 722-724. Click Applications: a. “Click Chemistry: Diverse Chemical Function form a Few Good Reactions,” H. C. Kolb, M.G. Finn, and K. Barry Sharpless, Angew. Chem., Int. Eng. Ed., 40, 2004-2021 (2001); b. “The growing impact of click chemistry on drug discovery,” H. C. Kolb and K. Barry Sharpless, Drug Discovery Today, 8(24), 128-1137 (2003); c. “CuI-Catalyzed Alkyne-Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective,” V. C. Bock, H. Hiemstra and J. H. van Maarseveen, Eur. J. Org. Chem., 51-68 (2006);; d. “A Rapid and Versatile Method to Label Receptor Ligands Using “Click” Chemistry: Validation with the Muscarinic M1 Antagonist Pirenzepine,” Bioconjugate Chemistry, 17, 1618-1623 (2006). Staudinger ligations: a. “The Staudinger Ligation-A Gift to Chemical Biology,” M. Kohn and R. Breinbauer, Angew. Chem. Int. Ed., 43, 3106 (2004); b. “Traceless Staudinger Ligation of Glycosyl Azides with Triaryl Phosphines: Stereoselective Synthesis of Glycosyl Amides,” A. Bianchi and A. Bernardi, J. Org. Chem., 71, 4565-4577 (2006); c. “Reaction Mechanism and Kinetics of the Traceless Staudinger Ligation,” M. Soelner, B. L. Nilsson and R. T. Raines, J. Amer. Chem. Soc., 128 (27), 8820-8828 (2006). The first reference is an excellent and recent review in a very active area. Search engines for “Staudinger ligation” for many excellent and additional references.