ABNOH-Linked Nucleotides and DNA for Bioconjugation and Cross-linking with Tryptophan-Containing Peptides and Proteins

0587190 - ÚOCHB 2025 RIV DE eng J - Článek v odborném periodiku
Spampinato, Ambra - Leone, Denise Liu - Pohl, Radek - Tarábek, Ján - Šoltysová, Markéta - Polák, Marek - Kádek, Alan - Sýkorová, Veronika - Řezáčová, Pavlína - Hocek, Michal
ABNOH-Linked Nucleotides and DNA for Bioconjugation and Cross-linking with Tryptophan-Containing Peptides and Proteins.
Chemistry - A European Journal. (2024), č. článku e202402151. ISSN 0947-6539. E-ISSN 1521-3765
Grant CEP: GA ČR(CZ) GX20-00885X; GA MŠMT(CZ) EH22_008/0004575
Výzkumná infrastruktura: CIISB III - 90242
Institucionální podpora: RVO:61388963 ; RVO:61388971
Klíčová slova: bioconjugation * DNA * proteins
Obor OECD: Biochemistry and molecular biology
Impakt faktor: 4.3, rok: 2022
Způsob publikování: Open access
https://doi.org/10.1002/chem.202402151

Reactive N-hydroxy-9-azabicyclo[3.3.1]nonane (ABNOH) linked 2’-deoxyuridine 5’-O-mono- and triphosphates were synthesized through a CuAAC click reaction of ABNO-H-PEG4-N3 with 5-ethynyl-dUMP or -dUTP. The modified triphosphate was used as substrate for enzymatic synthesis of modified DNA probes with KOD XL DNA polymerase. The keto-ABNO radical reacted with tryptophan (Trp) and Trp-containing peptides to form a stable 3-fused hexahydropyrrolo-indole conjugates. Similarly modified ABNO-H-linked nucleotides reacted with Trp-containing peptides to form a stable conjugate in the presence but surprisingly even in the absence of NaNO2 (presumably through activation by O2). The reactive ABNO-H-modified DNA probe was used for bioconjugations and crosslinking with Trp-containing peptides or proteins.
Trvalý link: https://hdl.handle.net/11104/0354457