Chemical synthesis of linear ADP-ribose oligomers up to pentamer and their binding to the oncogenic helicase ALC1

Liu, Qiang; Knobloch, G.; Voorneveld, Jim; Meeuwenoord, Nico J.; Overkleeft, Herman S.; Marel, Gijsbert A. van der; Ladurner, Andreas G.; Filippov, Dmitri V.

doi:10.1039/d1sc02340c

Chem. Sci.

2021

DOI: 10.1039/d1sc02340c

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Chemical synthesis of linear ADP-ribose oligomers up to pentamer and their binding to the oncogenic helicase ALC1

Qiang Liu

G. Knobloch

Jim Voorneveld

et al.

Abstract: ADP-ribosylation is a pivotal post-translational modification that mediates various important cellular processes producing negatively charged biopolymer, poly (ADP-ribose), the functions of which need further elucidation. Toward this end, the availability...

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References 37 publications

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Protecting‐Group‐Free Synthesis of ADP‐Ribose and Dinucleoside Di‐/Triphosphate Derivatives via P(V)‐P(V) Coupling Reaction

Hagino,

Kuwabara,

Komura

et al. 2024

Chemistry A European J

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Biomolecules containing adenosine di‐ or triphosphate (ADP or ATP) are crucial for diverse biological processes. Synthesis of these biomolecules and development of their chemical probes are important to elucidate their functions. Enabling reproducible and high‐yielding access to these ADP‐ and ATP‐containing molecules via conventional P(III)–P(V) and P(V)–P(V) coupling reactions is challenging owing to water content in highly polar phosphate‐containing substrates. Herein, we report an efficient and reliable method for protecting‐group‐free P(V)–P(V) coupling reaction through in situ activation of phosphates using hydrolysis‐stable 2‐[N‐(2‐methylimidazoyl)]‐1,3‐dimethylimidazolinium chloride (2‐MeImIm‐Cl), providing the corresponding electrophilic P(V) intermediates for subsequent nucleophilic attack using their coupling partners. This P(V)–P(V) coupling reaction proceeded even in a wet reaction medium and showed a broad substrate scope, accommodating protecting‐group‐free synthesis of ADP‐ribose and nicotinamide adenine diphosphate analogs, ATP‐containing biomolecules, and ADP‐ribosyl peptides.

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Protecting‐Group‐Free Synthesis of ADP‐Ribose and Dinucleoside Di‐/Triphosphate Derivatives via P(V)‐P(V) Coupling Reaction

Hagino,

Kuwabara,

Komura

et al. 2024

Chemistry A European J

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show abstract

The fast-growing business of Serine ADP-ribosylation

Longarini

Matić

2022

DNA Repair

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PARPs and ADP-ribosylation: Deciphering the complexity with molecular tools

Dasovich

Leung

2023

Molecular Cell

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Chemical synthesis of linear ADP-ribose oligomers up to pentamer and their binding to the oncogenic helicase ALC1

Abstract: ADP-ribosylation is a pivotal post-translational modification that mediates various important cellular processes producing negatively charged biopolymer, poly (ADP-ribose), the functions of which need further elucidation. Toward this end, the availability...

Cited by 3 publications

References 37 publications

Protecting‐Group‐Free Synthesis of ADP‐Ribose and Dinucleoside Di‐/Triphosphate Derivatives via P(V)‐P(V) Coupling Reaction

Protecting‐Group‐Free Synthesis of ADP‐Ribose and Dinucleoside Di‐/Triphosphate Derivatives via P(V)‐P(V) Coupling Reaction

The fast-growing business of Serine ADP-ribosylation

PARPs and ADP-ribosylation: Deciphering the complexity with molecular tools

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