Inverse electron demand Diels-Alder additions (IEDDA) between 1,2,4,5-tetrazines and olefins have recently found widespread application as a novel click chemistry scheme.
In particular, the catalyst-free IEDDA reaction between 3-NLS (3-norbornene-L-serine) and 3,6-di-2-pyridyl-1,2,4,5-tetrazine is a versatile alternative to CuAAC (copper-catalysed azide-alkyne cycloaddition) and thiol-Michael addition due to its exceptional kinetics (0.59 M-1s-1) (Fig. 1A) and selectivity[2-4].
3-NLS can be used as a linker group to connect the tetrazines with the substrate/functionality of your choice (Fig. 1B). Both the carboxylic acid and the amine functionalities on 3-NLS make it an ideal linker for the functionalization of diverse compounds by using amine-carboxylic acid coupling system.
|CLK-109-25||25 mg||165 €|
|CLK-109-100||100 mg||495 €|
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 Knall et al. (2013) Inverse electron demand Diels–Alder (iEDDA)-initiated conjugation: a (high) potential click chemistry scheme. Chem. Soc. Rev. 42:5131.
 Knall et al. (2014) Kinetic studies of inverse electron demand Diels-Alder reactions (iEDDA) of norbornenes and 3,6-dipyridin-2-yl-1,2,4,5-tetrazine. Tetrahedron Lett. 55 (34):4763.
 Lukesch (2019) Novel amino acids bearing a norbornene moiety. U.S. Patent WO2019016354A1.
 Pagel (2018) Inverse electron demand Diels–Alder (IEDDA) reactions in peptide chemistry. J. Pept. Sci. 25 (1):e3141.