Proximity Labeling pp 147-163 | Cite as
Proximity-Induced Bioorthogonal Chemistry Using Inverse Electron Demand Diels-Alder Reaction
Abstract
Bioorthogonal chemistry techniques enable the selective and targeted manipulation of living systems. In order to yield universally applicable techniques, it is of great importance for bioorthogonal reactions to take place rapidly, selectively, and with the formation of only benign side products. One of the reactions that match these criteria well is the inverse electron demand Diels-Alder reaction (DAinv) between tetrazines and strained dienophiles. However, even this prime technique comes with the disadvantage of its reactants having limited stability under physiological conditions. In our protocol, an unreactive and therefore stable DAinv diene/dienophile pair reacts rapidly using DNA hybridization as secondary rate-accelerating process. Due to the fluorogenicity of the presented tetrazine rhodamine conjugate, this method enables the selective screening and evaluation of reactant pairs for proximity-mediated bioorthogonal chemistry.
Key words
Inverse electron demand Diels-Alder reaction Bioorthogonal chemistry Fluorogenic probes DNA-templated chemistryNotes
Acknowledgments
R.W. acknowledges funding from the Deutsche Forschungsgemeinschaft DFG (SPP1623, WO 1888/1–2). We thank Dr. Achim Wieczorek for scientific advice.
References
- 1.Sletten EM, Bertozzi CR (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed 48(38):6974–6998CrossRefGoogle Scholar
- 2.Row RD, Prescher JA (2018) Constructing new bioorthogonal reagents and reactions. Acc Chem Res 51(5):1073–1081CrossRefGoogle Scholar
- 3.Oliveira BL, Guo Z, Bernardes GJL (2017) Inverse electron demand Diels-Alder reactions in chemical biology. Chem Soc Rev 46(16):4895–4950CrossRefGoogle Scholar
- 4.Blackman ML, Royzen M, Fox JM (2008) Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels−Alder reactivity. J Am Chem Soc 130(41):13518–13519CrossRefGoogle Scholar
- 5.Pipkorn R, Waldeck W, Didinger B, Koch M, Mueller G, Wiessler M, Braun K (2009) Inverse-electron-demand Diels-Alder reaction as a highly efficient chemoselective ligation procedure: Synthesis and function of a BioShuttle for temozolomide transport into prostate cancer cells. J Pept Sci 15(3):235–241CrossRefGoogle Scholar
- 6.Werther P, Möhler JS, Wombacher R (2017) A bifunctional fluorogenic rhodamine probe for proximity-induced bioorthogonal chemistry. Chem Eur J 23(72):18216–18224CrossRefGoogle Scholar
- 7.Šečkutė J, Yang J, Devaraj NK (2013) Rapid oligonucleotide-templated fluorogenic tetrazine ligations. Nucleic Acids Res 41(15):e148–e148CrossRefGoogle Scholar
- 8.Wu H, Alexander SC, Jin S, Devaraj NK (2016) A bioorthogonal near-infrared fluorogenic probe for mRNA detection. J Am Chem Soc 138(36):11429–11432CrossRefGoogle Scholar
- 9.Anzalone AV, Wang TY, Chen Z, Cornish VW (2013) A common diaryl ether intermediate for the gram-scale synthesis of oxazine and xanthene fluorophores. Angew Chem Int Ed 52(2):650–654CrossRefGoogle Scholar
- 10.Maiti D, Buchwald SL (2009) Orthogonal Cu-and Pd-based catalyst systems for the O-and N-arylation of aminophenols. J Am Chem Soc 131(47):17423–17429CrossRefGoogle Scholar
- 11.Eildal JN, Bach A, Dogan J, Ye F, Zhang M, Jemth P, Strømgaard K (2015) Rigidified clicked dimeric ligands for studying the dynamics of the PDZ1-2 supramodule of PSD-95. Chembiochem 16(1):64–69CrossRefGoogle Scholar
- 12.Wieczorek A, Werther P, Euchner J, Wombacher R (2017) Green-to far-red-emitting fluorogenic tetrazine probes–synthetic access and no-wash protein imaging inside living cells. Chem Sci 8:1506–1510CrossRefGoogle Scholar
- 13.Yang J, Karver MR, Li W, Sahu S, Devaraj NK (2012) Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine. Angew Chem 124(21):5312–5315CrossRefGoogle Scholar
- 14.Klapars A, Buchwald SL (2002) Copper-catalyzed halogen exchange in aryl halides: an aromatic Finkelstein reaction. J Am Chem Soc 124(50):14844–14845CrossRefGoogle Scholar