ArticleAngewandte Chemie (International ed. in English)2014
DNA-catalyzed lysine side chain modification.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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Who cites it
9 citing papers in PubMed, 21 citations in OpenAlex.
- Sequence-Dependent Acylation of Peptide Lysine Residues by DNAzymes.Chembiochem : a European journal of chemical biology · 2024Article
- DNA Catalysis: Design, Function, and Optimization.Molecules (Basel, Switzerland) · 2024Review
- In Vitro Selection of Deoxyribozymes for the Detection of RNA Modifications.Methods in molecular biology (Clifton, N.J.) · 2022Article
- DNAzymes for amine and peptide lysine acylation.Organic & biomolecular chemistry · 2021Article
- DNA-catalyzed glycosylation using aryl glycoside donors.Chemical communications (Cambridge, England) · 2016Article
- Catalytic DNA: Scope, Applications, and Biochemistry of Deoxyribozymes.Trends in biochemical sciences · 2016Review
- DNA Catalysis: The Chemical Repertoire of DNAzymes.Molecules (Basel, Switzerland) · 2015Review
- Pursuing DNA catalysts for protein modification.Accounts of chemical research · 2015Article
- An Efficient Catalytic DNA that Cleaves L-RNA.PloS one · 2015Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Catalyzing the covalent modification of aliphatic amino groups, such as the lysine (Lys) side chain, by nucleic acids has been challenging to achieve. Such catalysis will be valuable, for example, for the practical preparation of Lys-modified proteins. We previously reported the DNA-catalyzed modification of the tyrosine and serine hydroxy side chains, but Lys modification has been elusive. Herein, we show that increasing the reactivity of the electrophilic reaction partner by using 5'-phosphorimidazolide (5'-Imp) rather than 5'-triphosphate (5'-ppp) enables the DNA-catalyzed modification of Lys in a DNA-anchored peptide substrate. The DNA-catalyzed reaction of Lys with 5'-Imp is observed in an architecture in which the nucleophile and electrophile are not preorganized. In contrast, previous efforts showed that catalysis was not observed when Lys and 5'-ppp were used in a preorganized arrangement. Therefore, substrate reactivity is more important than preorganization in this context. These findings will assist ongoing efforts to identify DNA catalysts for reactions of protein substrates at lysine side chains.
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Registered trials
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