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

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

  • Nat Commun. 2020 Nov 5;11(1):5600. doi: 10.1038/s41467-020-19409-1.
Anlian Zhu 1,  Xin Li 2,  Lili Bai 1,  Gongming Zhu 1,  Yuanyang Guo 1,  Jianwei Lin 2,  Yiwen Cui 2,  Gaofei Tian 2,  Lihe Zhang 3,  Jianji Wang 1,  Xiang David Li 4,  Lingjun Li 5
Affiliations

Affiliations

  • 1 Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, 453007, Xinxiang, Henan, China.
  • 2 Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
  • 3 State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University, 100191, Beijing, China.
  • 4 Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China. xiangli@hku.hk.
  • 5 Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, 453007, Xinxiang, Henan, China. lingjunlee@htu.edu.cn.
PMID: 33154359 DOI: 10.1038/s41467-020-19409-1
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.

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