Biomimetic α-selective ribosylation enables two-step modular synthesis of biologically important ADP-ribosylated peptides

Anlian Zhu, Xin Li, Lili Bai, Gongming Zhu, Yuanyang Guo, Jianwei Lin, Yiwen Cui, Gaofei Tian, Lihe Zhang, Jianji Wang, Xiang David Li () and Lingjun Li ()
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Anlian Zhu: Henan Normal University
Xin Li: The University of Hong Kong
Lili Bai: Henan Normal University
Gongming Zhu: Henan Normal University
Yuanyang Guo: Henan Normal University
Jianwei Lin: The University of Hong Kong
Yiwen Cui: The University of Hong Kong
Gaofei Tian: The University of Hong Kong
Lihe Zhang: Peking University
Jianji Wang: Henan Normal University
Xiang David Li: The University of Hong Kong
Lingjun Li: Henan Normal University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract The α-type ADP-ribosylated peptides represent a class of important molecular tools in the field of protein ADP-ribosylation, however, they are difficult to access because of their inherent complicated structures and the lack of effective synthetic tools. In this paper, we present a biomimetic α-selective ribosylation reaction to synthesize a key intermediate, α-ADP-ribosyl azide, directly from native β-nicotinamide adenine dinucleotide in a clean ionic liquid system. This reaction in tandem with click chemistry then offers a two-step modular synthesis of α-ADP-ribosylated peptides. These syntheses can be performed open air in eppendorf tubes, without the need for specialized instruments or training. Importantly, we demonstrate that the synthesized α-ADP-ribosylated peptides show high binding affinity and desirable stability for enriching protein partners, and reactivity in post-stage poly ADP-ribosylations. Owing to their simple chemistry and multidimensional bio-applications, the presented methods may provide a powerful platform to produce general molecular tools for the study of protein ADP-ribosylation.

Date: 2020
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DOI: 10.1038/s41467-020-19409-1

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