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Chemical name: (3aS,4S,6aR)-N-[3-(11,12-Didehydrodibenz[b,f]azocin-5(6H)-yl)-3-oxopropyl]hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide // Synonyms: Biotin-Dibenzocyclooctyne
|Molecular weight:||502,63 g/mol|
This biotin derivative bears a terminal DBCO group. It can be used to prepare various biotinylated conjugates via Click Chemistry. Biotin can be subsequently detected e.g. via streptavidin or avidin. DBCO alkynes allow to perform click reactions with azide-modified targets without the use of heavy metal catalysis via a strain-promoted azide-alkyne click reaction (SPAAC).
High-Throughput “FP-Tag” Assay for the Identification of Glycosyltransferase Inhibitors; Z. Gao, O. G. Ovchinnikova, B.-S. Huang, F. Liu, D. E. Williams, R. J. Andersen, T. L. Lowary, C. Whitfield, S. G. Withers; J. Am. Chem. Soc. 2019; 141(6): 2201-2204. https://doi.org/10.1021/jacs.8b10940.
Site-Specific Dual Functionalization of Cysteine Residue in Peptides and Proteins with 2-Azidoacrylates; S. Ariyasu, H. Hayashi, B. Xing, S. Chiba; Bioconjugate Chem. 2017; 28(4): 897-902. https://doi.org/10.1021/acs.bioconjchem.7b00024.
Diazo Groups Endure Metabolism and Enable Chemoselectivity in Cellulo; K. A. Andersen, M. R. Aronoff, N. A. McGrath, R. T. Raines; J. Am. Chem. Soc. 2015; 137(7): 2412-2415. https://doi.org/10.1021/ja5095815.
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