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DBCO-containing Reagents for Copper-free Click Reactions
The strain-promoted or Cu(I)-free [2+3] cycloaddition strategy relies on the use of strained cyclooctynes. Their use decreases the activation energy for the cycloaddition click reaction, enabling it to be carried out without the need for catalysis at low temperatures with an efficiency greater than that of the Cu(I)-catalyzed ligation. |
The strain-promoted Click reaction and the so called Staudinger ligation (phosphine-azide) are competing technologies for chemoselective ligation. Both reactions are chemoselective and do not require copper, so both do not damage biomolecules. However, the rate of Staudinger ligation is about 100fold lower than the rate of the DBCO cycloaddition, which makes the Staudinger ligation hardly useful for studying dynamic biological systems. Only in cases where the speed of ligation is irrelevant, both reactions can be used with about equal efficiency.
DBCO-containing Chemical Modification Reagents
DBCO-containing reagents for introduction of functional groups, such as amines, carboxylic acids or NHS estersDBCO-containing Biotinylation Reagents
DBCO-containing reagents with various spacers for the introduction of Biotin moietiesDBCO-containing PEGylation Reagents
DBCO-PEG conjugates for PEGylation of azide-containing biopolymersDBCO-containing Spacers
Spacer and linker building blocks containing a DBCO moietyDBCO-containing Fluorescent Dyes
Various fluorescent dyes modified with a DBCO group for attachment to azidesDBCO-containing Nucleotides
Nucleotides containing a DBCO moiety for attachment to azidesDBCO-containing Phosphoramidites
Phosphoramidites containing a DBCO moiety for modification of oligonucleotides by attachment to azidesSelected references:
[1] Debets et al. (2010) Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition. Chem. Commun. 46:97.
[2] Bertozzi et al. (2010) Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones. J. Am. Chem. Soc. 132:3688.
[3] Bertozzi et al. (2009) Biorthogonal Chemistry: Fishing for selectivity in a sea of functionality. Angew. Chem. Int. Ed. 48:6974.
[4] Ning et al. (2008) Visualizing Metabolically Labeled Glycoconjugates of Living Cells by Copper-Free and Fast Huisgen Cycloadditions. Angew. Chem. Int. Ed. 47:2253.
[5] Bertozzi et al. (2007) Copper-free click chemistry for dynamic in vivo imaging. Proc. Natl. Acad. Sci. U.S.A. 104:16793.
[6] Bertozzi et al. (2006) A comparative study of bioorthogonal reactions with azides. Chem. Biol. 1:644.
[1] Debets et al. (2010) Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition. Chem. Commun. 46:97.
[2] Bertozzi et al. (2010) Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones. J. Am. Chem. Soc. 132:3688.
[3] Bertozzi et al. (2009) Biorthogonal Chemistry: Fishing for selectivity in a sea of functionality. Angew. Chem. Int. Ed. 48:6974.
[4] Ning et al. (2008) Visualizing Metabolically Labeled Glycoconjugates of Living Cells by Copper-Free and Fast Huisgen Cycloadditions. Angew. Chem. Int. Ed. 47:2253.
[5] Bertozzi et al. (2007) Copper-free click chemistry for dynamic in vivo imaging. Proc. Natl. Acad. Sci. U.S.A. 104:16793.
[6] Bertozzi et al. (2006) A comparative study of bioorthogonal reactions with azides. Chem. Biol. 1:644.