DBCO-TFP ester (QBD-11815)

Description

DBCO-TFP ester, product number QBD-11815, is the 2,3,5,6-tetrafluorophenyl (TFP) ester of an aza-dibenzocyclooctyne (DBCO) product used for strain-promoted azide-alkyne cycloaddition (SPAAC, also known as “”copper free click chemistry””). The TFP ester reacts selectively and efficiently with amines to form amide bonds. TFP esters are preferred over N-hydroxysuccinimide (NHS) esters because they are more stable to hydrolysis and react more efficiently with amines than NHS esters. The DBCO moiety reacts selectively with azides via SPAAC to form stable triazole linkages. Insoluble in water, DBCO-TFP ester is slightly soluble to sparingly soluble in most organic solvents. Vector Laboratories recommends dimethylsulfoxide (DMSO), N,N’-dimethylformamide (DMF), or N,N’-dimethylacetamide (DMAC) as solvents for this product. DBCO-TFP ester is acid sensitive. It should not be subjected to pH <5 during reaction or workup.

The published discovery in 2004 of SPAAC, also known as “”copper free click chemistry,”” by Carolyn Bertozzi and coworkers improved the click chemistry toolbox. Toxic copper catalysts were eliminated, making the reaction truly bioorthogonal. By removing the copper(I) catalyst from the reaction, living cells can be labeled with reagents designed for SPAAC. Since the original publication, multiple improvements in strained cyclooctyne reagents resulted in the development of DBCO as a nearly perfect azide partner for SPAAC.

To use DBCO-TFP ester in aqueous media or in cells, it should be conjugated to a water-soluble dPEG® product. Vector Laboratories offers numerous products for this purpose, including amino alcohols and amino acids. We also offer many ready-to-use DBCO-functionalized dPEG® products.

Specifications

Documents

References

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). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.

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.