Synthesis 2015; 47(18): 2738-2744
DOI: 10.1055/s-0034-1380721
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Evaluation of Nicotinic Acid Derived Tetrazines for Bioorthogonal Labeling

Gergely B. Cserép
a  Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary   Email: kele.peter@ttk.mta.hu
,
Orsolya Demeter
a  Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary   Email: kele.peter@ttk.mta.hu
,
Effi Bätzner
b  Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany   Email: Wagenknecht@kit.edu
,
Mihály Kállay
c  MTA-BME ‘Lendület’ Quantum Chemistry Research Group, Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, P. O. Box 91, 1521 Budapest, Hungary
,
Hans-Achim Wagenknecht*
b  Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany   Email: Wagenknecht@kit.edu
,
Péter Kele*
a  Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary   Email: kele.peter@ttk.mta.hu
› Author Affiliations
Further Information

Publication History

Received: 11 March 2015

Accepted: 16 April 2015

Publication Date:
27 May 2015 (eFirst)

Abstract

A set of nicotinic acid derived tetrazines were synthesized and evaluated for activity in inverse-electron-demand Diels–Alder (IEDDA­) reactions with various dienophiles. It was found that the performance of these tetrazines is governed by two factors. Theoretical and experimental investigations showed that steric effects may override the energetically predicted order of reactivity. Making a compromise between reactivity and stability, a selected tetrazine was incorporated into a deoxynucleotide to afford a bioorthogonalized building block enabling IEDDA-based tagging schemes of nucleic acids.

Supporting Information

 
  • References

  • 1 These two authors contributed equally to the work.
  • 2 Knall A.-C, Slugovc C.  Chem. Soc. Rev. 2013;  42: 5131
  • 3 Bußkamp H, Batroff E, Niederwieser A, Abdel-Rahman OS, Winter RF, Wittmann V, Marx A. Chem. Commun. 2014; 50: 10827
  • 4 Rieder U, Luedtke NW. Angew. Chem. Int. Ed. 2014; 53: 9168
    • 5a Schoch J, Ameta S, Jäschke A. Chem. Commun. 2011; 47: 12356
    • 5b Asare-Okai PN, Augustin E, Fabris D, Royzen M. Chem. Commun. 2014; 50: 7844
    • 5c Pyka AM, Domnick C, Braun F, Kath-Schorr S. Bioconjugate Chem. 2014; 25: 1438
    • 5d Ameta S, Becker J, Jäschke A. Org. Biomol. Chem. 2014; 12: 4701
  • 6 Nikić I, Plass T, Schraidt O, Szymański J, Briggs JA, Schultz C, Lemke EA. Angew. Chem. Int. Ed. 2014; 53: 2245
  • 7 Schoch J, Staudt M, Samanta A, Wiessler M, Jäschke A. Bioconjugate Chem. 2012; 23: 1382
  • 8 Wijnen J, Zavarise S, Engberts J, Charton M. J. Org. Chem. 1996; 61: 2001
  • 9 Geldard J, Lions F. J. Org. Chem. 1965; 30: 318
  • 10 Hoeben FJ. M, Robillard MS, Rossin R, Ten HW, Versteegen RM. PCT Int. Appl WO 2012156920, 2012
  • 11 Agard N, Baskin J, Prescher J, Lo A, Bertozzi C. ACS Chem. Biol. 2006; 1: 644
  • 12 Becke A. J. Chem. Phys. 1993; 98: 5648
  • 13 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision B.01 . Gaussian, Inc; Wallingford CT: 2009
  • 14 Stubinitzky C, Cserép GB, Bätzner E, Kele P, Wagenknecht H.-A. Chem. Commun. 2014; 50: 11218
  • 15 Varga BR, Kállay M, Hegyi K, Béni S, Kele P. Chem. Eur. J. 2012; 18: 822
  • 16 Royzen M, Yap G, Fox J.  J. Am. Chem. Soc. 2008; 130: 3760
  • 17 Dommerholt J, Schmidt S, Temming R, Hendriks L, Rutjes F, van Hest J, Lefeber D, Friedl P, van Delft F. Angew. Chem. Int. Ed. 2010; 49: 9422
  • 18 Lang K, Davis L, Wallace S, Mahesh M, Cox D, Blackman M, Fox J, Chin J. J. Am. Chem. Soc. 2012; 134: 10317
  • 19 Bergen K, Steck A.-L, Schütt S, Baccaro A, Welte W, Diederichs K, Marx A. J. Am. Chem. Soc. 2012; 134: 11840
    • 20a Battersby T, Ang D, Burgstaller P, Jurczyk S, Bowser M, Buchanan D, Kennedy R, Benner S.  J. Am. Chem. Soc. 1999; 121: 9781
    • 20b Brazier JA, Shibata T, Townsley J, Taylor BF, Frary E, Williams NH, Williams DM. Nucleic Acids Res. 2005; 33: 1362
    • 20c Nuzzolo M, Grabulosa A, Slawin A, Meeuwenoord N, Marel G, Kamer P. Eur. J. Org. Chem. 2010; 3229
  • 21 Sakamoto T, Kaneda S-I, Nishimura S, Yamanaka H. Chem. Pharm. Bull. 1985; 33: 565