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Bio-Labeling: Fast Click of 3-NLS with Tetrazines

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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[1].

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.

Figure 1. A) IEDDA reaction of 3-norbornene-L-serine with 3,6-di-2-pyridyl-1,2,4,5-tetrazine. B) 3-norbornene-L-serine as a linker group to connect the tetrazines with the substrate/functionality of your choice. R=H, CH3.

Figure 1: A) IEDDA reaction of 3-NLS with 3,6-di-2-pyridyl-1,2,4,5-tetrazine. B) 3-NLS as a linker group to connect the tetrazines with the substrate/functionality of your choice. R = H, CH3.

Product Cat.-No. Amount Price
3-Norbornene-L-serine
(3-NLS)
CLK-109-25 25 mg 165 €
CLK-109-100 100 mg 495 €

Questions or inquiries?

Dr. Jana Balintova

Please contact Jana with all questions or inquiries you may have!

Selected References:

[1] Knall et al. (2013) Inverse electron demand Diels–Alder (iEDDA)-initiated conjugation: a (high) potential click chemistry scheme. Chem. Soc. Rev. 42:5131.
[2] 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.
[3] Lukesch (2019) Novel amino acids bearing a norbornene moiety. U.S. Patent WO2019016354A1.
[4] Pagel (2018) Inverse electron demand Diels–Alder (IEDDA) reactions in peptide chemistry. J. Pept. Sci. 25 (1):e3141.