Polymerase Synthesis of DNA Containing Iodinated Pyrimidine or 7-Deazapurine Nucleobases and Their Post-synthetic Modifications through the Suzuki-Miyaura Cross-Coupling Reactions

0552855 - ÚOCHB 2023 RIV DE eng J - Článek v odborném periodiku
Sýkorová, Veronika - Tichý, Michal - Hocek, Michal
Polymerase Synthesis of DNA Containing Iodinated Pyrimidine or 7-Deazapurine Nucleobases and Their Post-synthetic Modifications through the Suzuki-Miyaura Cross-Coupling Reactions.
Chembiochem. Roč. 23, č. 3 (2022), č. článku e202100608. ISSN 1439-4227. E-ISSN 1439-7633
Grant CEP: GA ČR(CZ) GA18-03305S
Grant ostatní: AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institucionální podpora: RVO:61388963
Klíčová slova: nucleotides * DNA * oligonucleotides * bioconjugations * cross-coupling reactions
Obor OECD: Organic chemistry
Impakt faktor: 3.2, rok: 2022
Způsob publikování: Omezený přístup
https://doi.org/10.1002/cbic.202100608

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.
Trvalý link: http://hdl.handle.net/11104/0327950