QBD 11815

DBCO-TFP ester

$247.00 – $1,339.00

El éster DBCO-TFP, número de producto 11815, es el éster de 2,3,5,6-tetrafluorofenilo (TFP) de un producto de aza-dibenzociclooctino (DBCO) utilizado para la cicloadición de azida-alquino promovida por deformación (SPAAC, también conocida como “” química de clic libre de cobre””). El éster de TFP reacciona selectiva y eficientemente con aminas para formar enlaces amida. Los ésteres de TFP se prefieren a los ésteres de N-hidroxisuccinimida (NHS) porque son más estables a la hidrólisis y reaccionan más eficientemente con las aminas que los ésteres de NHS. El resto DBCO reacciona selectivamente con azidas a través de SPAAC para formar enlaces triazol estables. Insoluble en agua, el éster DBCO-TFP es de ligeramente soluble a escasamente soluble en la mayoría de los disolventes orgánicos. Vector Laboratories recomienda dimetilsulfóxido (DMSO), N,N’-dimetilformamida (DMF) o N,N’-dimetilacetamida (DMAC) como disolventes para este producto. El éster DBCO-TFP es sensible a los ácidos. No debe someterse a un pH <5 durante la reacción o el procesamiento.

El descubrimiento publicado en 2004 de SPAAC, también conocido como “química de clic sin cobre”, por Carolyn Bertozzi y sus compañeros de trabajo mejoró la caja de herramientas de la química de clic. Se eliminaron los catalizadores de cobre tóxicos, lo que hizo que la reacción fuera verdaderamente bioortogonal. Al eliminar el catalizador de cobre (I) de la reacción, las células vivas se pueden marcar con reactivos diseñados para SPAAC. Desde la publicación original, múltiples mejoras en los reactivos de ciclooctina filtrados dieron como resultado el desarrollo de DBCO como un socio de azida casi perfecto para SPAAC.

Para utilizar el éster DBCO-TFP en medios acuosos o en células, se debe conjugar con un producto dPEG® soluble en agua. Vector Laboratories ofrece numerosos productos para este fin, incluidos aminoalcoholes y aminoácidos. También ofrecemos muchos productos dPEG® funcionalizados con DBCO listos para usar.

Specifications

Unit Size 100 mg, 1000 mg
Molecular Weight 467.41; single compound
Chemical formula C₂₆H₁₇F₄NO₃
CAS N/A
Purity > 98%
Spacers N/A
Shipping Ambient
Typical solubility properties (for additional information contact Customer Support) Methylene Chloride, Chloroform, DMSO, DMAC, or DMF.
Storage and handling -20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

 

SKU: QBD-11815 Category: Tags: , ,

Description

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

Unit Size 100 mg, 1000 mg
Molecular Weight 467.41; single compound
Chemical formula C₂₆H₁₇F₄NO₃
CAS N/A
Purity > 98%
Spacers N/A
Shipping Ambient
Typical solubility properties (for additional information contact Customer Support) Methylene Chloride, Chloroform, DMSO, DMAC, or DMF.
Storage and handling -20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

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.

Additional information

Weight 1 oz

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