All four iodinated 2'-deoxyribonucleoside triphosphates (dNTPs) derived from 5-iodouracil, 5-iodocytosine, 7-iodo-7-deazaadenine and 7-iodo-7-deazaguanine were prepared and studied as substrates for KOD XL DNA polymerase. All of the nucleotides were readily incorporated by primer extension and by PCR amplification to form DNA containing iodinated nucleobases. Systematic study of the Suzuki-Miyaura cross-coupling reactions with two bulkier arylboronic acids revealed that the 5-iodopyrimidines were more reactive and gave cross-coupling products both in the terminal or internal position in single-stranded oligonucleotides (ssONs) and in the terminal position of double-stranded DNA (dsDNA), whereas the 7-iodo-7-deazapurines were less reactive and gave cross-coupling products only in the terminal position. None of the four iodinated bases reacted in an internal position of dsDNA. These findings are useful for the use of the iodinated nucleobases for post-synthetic modification of DNA with functional groups for various applications.

Department of Organic Chemistry Faculty of Science Charles University Prague Hlavova 8 12843 Prague 2 Czech Republic

Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo nam 2 16610 Prague 6 Czech Republic

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H. G. Gratzner, Science 1982, 218, 474-475.

B. Michalska, I. Sobolewski, K. Polska, J. Zielonka, A. Zylicz-Stachula, P. Skowron, J. Rak, J. Pharm. Biomed. Anal. 2011, 56, 671-677.

P. Wityk, M. Zdrowowicz, J. Wiczk, J. Rak, J. Pharm. Biomed. Anal. 2017, 142, 262-269.

K. Westphal, M. Zdrowowicz, A. Zylicz-Stachula, J. Rak, J. Photochem. Photobiol. B 2017, 167, 228-235.

T. Watanabe, T. Bando, Y. Xu, R. Tashiro, H. Sugiyama, J. Am. Chem. Soc. 2005, 127, 44-45.

T. Watanabe, R. Tashiro, H. Sugiyama, J. Am. Chem. Soc. 2007, 129, 8163-8168.

F. Hashiya, A. Saha, S. Kizaki, Y. Li, H. Sugiyama, Nucleic Acids Res. 2014, 42, 13469-13473.

E. E. Blatter, Y. W. Ebright, R. H. Ebright, Nature 1992, 359, 650-652.

M. C. Willis, B. J. Hicke, O. C. Uhlenbeck, T. R. Cech, T. H. Koch, Science 1993, 262, 1255-1257.

J. Liu, M. Sodeoka, W. S. Lane, G. L. Verdine, Proc. Natl. Acad. Sci. USA 1994, 91, 908-912.

M. Mücke, V. Pingoud, G. Grelle, R. Kraft, D. H. Krüger, M. Reuter, J. Biol. Chem. 2002, 277, 14288-14293.

B. Holz, N. Dank, J. E. Eickhoff, G. Lipps, G. Krauss, E. Weinhold, J. Biol. Chem. 1999, 274, 15066-15072.

V. A. Malkov, I. Biswas, R. D. Camerini-Otero, P. Hsieh, J. Biol. Chem. 1997, 272, 23811-23817.

V. Pingoud, H. Thole, F. Christ, W. Grindl, W. Wende, A. Pingoud, J. Biol. Chem. 1999, 274, 10235-10243.

E. A. Kubareva, H. Thole, A. S. Karyagina, T. S. Oretskaya, A. Pingoud, V. Pingoud, Nucleic Acids Res. 2000, 28, 1085-1091.

M.-E. Dextraze, S. Cecchini, F. Bergeron, S. Girouard, K. Turcotte, J. R. Wagner, D. J. Hunting, Biochemistry 2009, 48, 2005-2011.

Y. Zeng, Y. Wang, J. Am. Chem. Soc. 2004, 126, 6552-6553.

T. Chen, G. P. Cook, A. T. Koppisch, M. M. Greenberg, J. Am. Chem. Soc. 2000, 122, 3861-3866.

G. P. Cook, M. M. Greenberg, J. Am. Chem. Soc. 1996, 118, 10025-10030.

F. Seela, M. Zulauf, Chem. Eur. J. 1998, 4, 1781-1790.

F. Seela, N. Ramzaeva, Y. Chen, Bioorg. Med. Chem. Lett. 1995, 5, 3049-3052.

N. Ramzaeva, F. Seela, Helv. Chim. Acta 1996, 79, 1549-1558.

E. Ferrer, M. Wiersma, B. Kazimierczak, C. W. Müller, R. Eritja, Bioconjugate Chem. 1997, 8, 757-761.

J. Bodnarz, W. Zempsky, D. Warder, C. Bergson, D. Ward, J. Biol. Chem. 1983, 258, 5206-5213.

K. He, K. W. Porter, A. Hasan, J. D. Briley, B. R. Shaw, Nucleic Acids Res. 1999, 27, 1788-1794.

O. I. Lavrik, A. L. Zakharenko, R. Prasad, V. A. Vlasov, V. S. Bogachev, A. Favre, Mol. Biol. 1998, 32, 510-517.

M. G. McDougall, L. P. Hosta, S. Kumar, C. W. Fuller, Nucleosides Nucleotides 1999, 18, 1009-1011.

M. G. McDougall, L. Sun, I. Livshin, L. P. Hosta, B. F. McArdle, S. B. Samols, C. W. Fuller, S. Kumar, Nucleosides Nucleotides Nucleic Acids 2001, 20, 501-506.

G. Hervé, G. Sartori, G. Enderlin, G. Mackenzie, C. Len, RSC Adv. 2014, 4, 18558.

K. H. Shaughnessy, Molecules 2015, 20, 9419-9454.

E. Defrancq, S. Messaoudi, ChemBioChem 2017, 18, 426-431.

S. I. Khan, M. W. Grinstaff, J. Am. Chem. Soc. 1999, 121, 4704-4705.

M. Rist, N. Amann, H.-A. Wagenknecht, Eur. J. Org. Chem. 2003, 2498-2504.

M. Ejlersen, C. Lou, Y. S. Sanghvi, Y. Tor, J. Wengel, Chem. Commun. 2018, 54, 8003-8006.

A. Omumi, D. G. Beach, M. Baker, W. Gabryelski, R. A. Manderville, J. Am. Chem. Soc. 2011, 133, 42-50.

H. Cahová, A. Jäschke, Angew. Chem. Int. Ed. 2013, 52, 3186-3190;

Angew. Chem. 2013, 125, 3268-3272.

L. Lercher, J. F. McGouran, B. M. Kessler, C. J. Schofield, B. G. Davis, Angew. Chem. Int. Ed. 2013, 52, 10553-10558;

Angew. Chem. 2013, 125, 10747-10752.

M. B. Walunj, A. A. Tanpure, S. G. Srivatsan, Nucleic Acids Res. 2018, 46, e65;

M. B. Walunj, S. G. Srivatsan, Methods Mol. Biol. 2020, 2166, 473-486.

M. B. Walunj, S. G. Srivatsan, Bioconjugate Chem. 2020, 31, 2513-2521.

P. Capek, H. Cahová, R. Pohl, M. Hocek, C. Gloeckner, A. Marx, Chem. Eur. J. 2007, 13, 6196-6203.

B. H. Le, J. C. Koo, H. N. Joo, Y. J. Seo, Bioorg. Med. Chem. 2017, 25, 3591-3596.

H. Cahová, L. Havran, P. Brázdilová, H. Pivonková, R. Pohl, M. Fojta, M. Hocek, Angew. Chem. Int. Ed. 2008, 47, 2059-2062;

Angew. Chem. 2008, 120, 2089-2092.

P. Güixens-Gallardo, M. Hocek, P. Perlíková, Bioorg. Med. Chem. Lett. 2016, 26, 288-291.

P. Ménová, D. Dziuba, P. Güixens-Gallardo, P. Jurkiewicz, M. Hof, M. Hocek, Bioconjugate Chem. 2015, 26, 361-366.

P. Brázdilová, M. Vrábel, R. Pohl, H. Pivonková, L. Havran, M. Hocek, M. Fojta, Chem. Eur. J. 2007, 13, 9527-9533.

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