Description

DBCO-acid, product number QBD-11814, is an aza-dibenzocyclooctyne (DBCO) product used for strain-promoted azide-alkyne cycloaddition (SPAAC, also known as “”copper free click chemistry””). The DBCO moiety reacts selectively with azides via SPAAC to form stable triazole linkages. Esterification of the terminal carboxylic acid with N-hydroxysuccinimide (NHS) or 2,3,5,6-tetrafluorophenol (TFP) allows for reaction with a primary amine. Insoluble in water, DBCO-acid 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-acid is relatively insensitive to bases and can be used in the presence of aqueous bases. This product is acid sensitive and 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-acid 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 DBCO-based dPEG® products already prepared for use.

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.

Description

m-dPEG®12-DBCO, product number QBD-10596, is a methoxy-terminated, discrete polyethylene glycol (dPEG®) click chemistry reagent designed for chemical modification of surfaces through strain-promoted azide-alkyne cycloaddition (SPAAC). From the terminal methyl group to the reactive site on the dibenzylcyclooctyne (DBCO) group, the dPEG® spacer is 39 atoms long.

DBCO was designed for bio-orthogonal click chemistry applications using SPAAC, also known as copper-free click chemistry, which was developed by Carolyn Bertozzi and colleagues to avoid the potential toxicity of Cu(I) that is used in Copper(I)-Promoted Azide Alkyne Cycloaddition (CuAAC) discovered by K. Barry Sharpless and colleagues. The dPEG® spacer differs from traditional PEG spacers and linkers in that it consists of a single molecular weight and chain length of PEG (i.e., it is monodispersed), which simplifies analysis of conjugates made with this compound.

Potential uses for this product include modifying alkyne-functionalized surfaces and peptides and proteins containing alkyne-functionalized amino acid side chains.

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.

Description

m-dPEG®24-DBCO, product number QBD-10583, is a methoxy-terminated, discrete polyethylene glycol (dPEG®) click chemistry reagent designed for chemical modification of surfaces through strain-promoted azide-alkyne cycloaddition (SPAAC). From the terminal methyl group to the reactive site on the dibenzylcyclooctyne (DBCO) group, the dPEG® spacer is 83 atoms long.

DBCO was designed for bio-orthogonal click chemistry applications using SPAAC, also known as copper-free click chemistry, which was developed by Carolyn Bertozzi and colleagues to avoid the potential toxicity of Cu(I) that is used in Copper(I)-Promoted Azide Alkyne Cycloaddition (CuAAC) discovered by K. Barry Sharpless and colleagues. The dPEG® spacer differs from traditional PEG spacers and linkers in that it consists of a single molecular weight and chain length of PEG (i.e., it is monodispersed), which simplifies analysis of conjugates made with this compound.

Potential uses for this product include modifying alkyne-functionalized surfaces and peptides and proteins containing alkyne-functionalized amino acid side chains.

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.