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ABNOH-Linked Nucleotides and DNA for Bioconjugation and Cross-linking with Tryptophan-Containing Peptides and Proteins.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Sep 02; Vol. 30 (49), pp. e202402151. Date of Electronic Publication: 2024 Aug 12. - Publication Year :
- 2024
-
Abstract
- Reactive N-hydroxy-9-azabicyclo[3.3.1]nonane (ABNOH) linked 2'-deoxyuridine 5'-O-mono- and triphosphates were synthesized through a CuAAC reaction of ABNOH-PEG <subscript>4</subscript> -N <subscript>3</subscript> 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 tricyclic fused hexahydropyrrolo-indole conjugates. Similarly modified ABNOH-linked nucleotides reacted with Trp-containing peptides to form a stable conjugate in the presence but surprisingly even in the absence of NaNO <subscript>2</subscript> (presumably through activation by O <subscript>2</subscript> ). The reactive ABNOH-modified DNA probe was used for bioconjugations and crosslinking with Trp-containing peptides or proteins.<br /> (© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 30
- Issue :
- 49
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 38924659
- Full Text :
- https://doi.org/10.1002/chem.202402151