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

DBCO-amine, product number QBD-11750, 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. The amine terminus of the molecule reacts with carboxylic acids and their active esters to form stable amide bonds. Insoluble in water, DBCO-amine 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-amine is relatively insensitive to bases and can be used in the presence of aqueous bases. This product is acid sensitive. It should not be subjected to pH <5 during reaction or workup. The product should always be stored at -20°C when not in use.

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-amine effectively 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 hydroxy acids (and their active esters), and protected 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

Bis-dPEG®11-DBCO, product number QBD-11372, is a homobifunctional click chemistry crosslinker consisting of two dibenzylcyclooctyne (DBCO) groups separated by a medium-length (39 atoms, 44.2 Å), single molecular weight, discrete polyethylene glycol (dPEG®) spacer. The DBCO groups react with azide groups via the bioorthogonal click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry. This product is particularly useful for click chemistry reactions where the presence or use of copper(I) [Cu(I)] is undesirable. Any two molecules containing accessible azide groups can be crosslinked with this compound. Applications for Bis-dPEG®11-DBCO include crosslinking biomolecules that have been modified to include azide groups and construction of complex supramolecular structures.

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

DBCO-dPEG®24-TFP ester, product number QBD-11370, is a heterobifunctional, bioorthogonal crosslinker designed to join azides and amines across a long (76 atoms, 88.8 Å), flexible, hydrophilic, single molecular weight, discrete PEG (dPEG®) spacer. The tetrafluorophenyl (TFP) ester reacts specifically with free amines to form amide bonds; the optimum reaction pH is 7.5 – 8.0. The dibenzylcyclooctyne (DBCO) moiety selectively forms triazole linkages with azides via a click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry. The amphiphilic dPEG® linker increases conjugates’ hydrodynamic volumes, and it can be used to create space in sterically crowded supramolecular constructs.

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

DBCO-dPEG®12-TFP ester, product number QBD-11366, is a heterobifunctional, bioorthogonal crosslinker designed to join azides and amines across a medium-length (40 atoms, 46.3 Å), flexible, hydrophilic, single molecular weight, discrete PEG (dPEG®) spacer. The tetrafluorophenyl (TFP) ester reacts specifically with free amines to form amide bonds; the optimum reaction pH is 7.5 – 8.0. The dibenzylcyclooctyne (DBCO) moiety selectively forms triazole linkages with azides via a click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry. The amphiphilic dPEG® linker increases conjugates’ hydrodynamic volumes, and it can be used to create space in sterically crowded supramolecular constructs.

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

DBCO-dPEG®4-TFP ester, product number QBD-11362, is a heterobifunctional, bioorthogonal crosslinker designed to join azides and amines across a short (16 atoms, 17.9 Å), flexible, hydrophilic, single molecular weight, discrete PEG (dPEG®) spacer. The tetrafluorophenyl (TFP) ester reacts specifically with free amines to form amide bonds; the optimum reaction pH is 7.5 – 8.0. The dibenzylcyclooctyne (DBCO) moiety selectively forms triazole linkages with azides via a click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry. The amphiphilic dPEG® linker increases conjugates’ hydrodynamic volumes, and it can be used to create space in sterically crowded supramolecular constructs.

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

DBCO-dPEG®36-TFP ester, product number QBD-10598, is a heterobifunctional, bioorthogonal crosslinker designed to join azides and amines across a long (122 atoms, 137.5 Å), flexible, hydrophilic, single molecular weight, discrete PEG (dPEG®) spacer. The tetrafluorophenyl (TFP) ester reacts specifically with free amines to form amide bonds; the optimum reaction pH is 7.5 – 8.0. The dibenzylcyclooctyne (DBCO) moiety selectively forms triazole linkages with azides via a click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry. The amphiphilic dPEG® linker increases conjugates’ hydrodynamic volumes and water solubility, and it can be used to create space in sterically crowded supramolecular constructs.

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

DBCO-dPEG®24-MAL, product number QBD-10594, is a long (90 atoms), single molecular weight, discrete polyethylene glycol (dPEG®) crosslinking reagent. The dibenzylcyclooctyne (DBCO) moiety permits strain promoted azide-alkyne cycloaddition (SPAAC), also known as “”copper free click chemistry.”” The maleimidopropyl (MAL) functional group forms a thiol-ether linkage with sulfhydryl groups. The hydrophilic, non-immunogenic dPEG® spacer in DBCO-dPEG®24-MAL provides the benefits of PEG (increased water solubility, non-immunogenicity) without the analytical headaches of PEG dispersity.

The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) discovered by K. Barry Sharpless and coworkers is one of the best known click chemistry reactions, but its in vivo usability is limited by copper toxicity. Carolyn Bertozzi and coworkers developed SPAAC as a way to avoid copper’s toxic effects on living cells using a highly strained cyclooctyne. Developments since the initial publication show that reagents based on DBCO provide excellent, highly selective reactivity with azides, forming a triazole product.

Maleimide groups are widely popular for their ability to react rapidly with sulfhydryl groups via a Michael addition to form thioether bonds.
Vector Laboratories’ dPEG® products clearly differ from traditional, polymeric polyethylene glycol (PEG). Traditional PEG is a disperse polymer product with a Poisson distribution of chain lengths and molecular weights. The intractable mixture of chain lengths and molecular weights in traditional PEG products creates significant analytical challenges. In contrast, Vector Laboratories’ dPEG® products are single molecular weight compounds with discrete chain lengths. Using Vector Laboratories’ products greatly simplifies analysis of dPEG®-conjugated compounds.

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

DBCO-dPEG®12-MAL, product number QBD-10593, is a medium-length (54 atoms), single molecular weight, discrete polyethylene glycol (dPEG®) crosslinking reagent. The dibenzylcyclooctyne (DBCO) moiety permits strain-promoted azide-alkyne cycloaddition (SPAAC), also known as “”copper-free click chemistry.”” The maleimidopropyl (MAL) functional group forms a thiol-ether linkage with sulfhydryl groups. The single molecular weight dPEG® spacer is hydrophilic and non-immunogenic. DBCO-dPEG®12-MAL provides the benefits of PEG (increased water solubility, non-immunogenicity) without the analytical headaches of PEG dispersity.

The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) discovered by K. Barry Sharpless and coworkers is one of the best-known click chemistry reactions, but its in vivo usability is limited by copper toxicity. Carolyn Bertozzi and coworkers developed SPAAC as a way to avoid copper’s toxic effects on living cells using a highly strained cyclooctyne. Developments since the initial publication show that reagents based on DBCO provide excellent, highly selective reactivity with azides, forming a triazole product.

Maleimide groups are widely popular for their ability to react rapidly with sulfhydryl groups via a Michael addition to form thioether bonds.

Vector Laboratories’ dPEG® products clearly differ from traditional polymeric polyethylene glycol (PEG). Traditional PEG is a dispersed polymer product with a Poisson distribution of chain lengths and molecular weights. The intractable mixture of chain lengths and molecular weights in traditional PEG products creates significant analytical challenges. In contrast, Vector Laboratories’ dPEG® products are single molecular weight compounds with discrete chain lengths. Using Vector Laboratories’ products greatly simplifies the analysis of dPEG®-conjugated compounds.

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

DBCO-dPEG®4-MAL, product number QBD-10592, is a short, single molecular weight, discrete polyethylene glycol (dPEG®) crosslinking reagent. The dibenzylcyclooctyne (DBCO) moiety permits strain-promoted azide-alkyne cycloaddition (SPAAC), also known as “”copper-free click chemistry.”” The maleimidopropyl (MAL) functional group forms a thiol-ether linkage with sulfhydryl groups. The short, single molecular weight dPEG® spacer is hydrophilic and non-immunogenic. DBCO-dPEG®4-MAL provides the benefits of PEG (increased water solubility, non-immunogenicity) without the analytical headaches of PEG dispersity.

The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) discovered by K. Barry Sharpless and coworkers is one of the best-known click chemistry reactions, but its in vivo usability is limited by copper toxicity. Carolyn Bertozzi and coworkers developed SPAAC as a way to avoid copper’s toxic effects on living cells using a highly strained cyclooctyne. Developments since the initial publication show that reagents based on DBCO provide excellent, highly selective reactivity with azides, forming a triazole product.

Maleimide groups are widely popular for their ability to react rapidly with sulfhydryl groups via a Michael addition to form thioether bonds.

Vector Laboratories’ dPEG® products clearly differ from traditional polymeric polyethylene glycol (PEG). Traditional PEG is a dispersed polymer product with a Poisson distribution of chain lengths and molecular weights. The intractable mixture of chain lengths and molecular weights in traditional PEG products creates significant analytical challenges. In contrast, Vector Laboratories’ dPEG® products are single molecular weight compounds with discrete chain lengths. Using Vector Laboratories’ products greatly simplifies the analysis of dPEG®-conjugated compounds.

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.