ADP-ribosyl-N₃: A Versatile Precursor for Divergent Syntheses of ADP-ribosylated Compounds

Lingjun Li; Qianqian Li; Shengqiang Ding; Pengyang Xin; Yuqin Zhang; Shenlong Huang; Guisheng Zhang

doi:10.3390/molecules22081346

ADP-ribosyl-N₃: A Versatile Precursor for Divergent Syntheses of ADP-ribosylated Compounds

Molecules. 2017 Aug 14;22(8):1346. doi: 10.3390/molecules22081346.

Authors

Lingjun Li¹, Qianqian Li², Shengqiang Ding³, Pengyang Xin⁴, Yuqin Zhang⁵, Shenlong Huang⁶, Guisheng Zhang⁷

Affiliations

¹ Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering Henan Normal University, Xinxiang 453007, Henan, China. [email protected].
² Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering Henan Normal University, Xinxiang 453007, Henan, China. [email protected].
³ Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering Henan Normal University, Xinxiang 453007, Henan, China. [email protected].
⁴ Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering Henan Normal University, Xinxiang 453007, Henan, China. [email protected].
⁵ Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering Henan Normal University, Xinxiang 453007, Henan, China. [email protected].
⁶ Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering Henan Normal University, Xinxiang 453007, Henan, China. [email protected].
⁷ Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering Henan Normal University, Xinxiang 453007, Henan, China. [email protected].

Abstract

Adenosine diphosphate-ribose (ADP-ribose) and its derivatives play important roles in a series of complex physiological procedures. The design and synthesis of artificial ADP-ribosylated compounds is an efficient way to develop valuable chemical biology tools and discover new drug candidates. However, the synthesis of ADP-ribosylated compounds is currently difficult due to structural complexity, easily broken pyrophosphate bond and high hydrophilicity. In this paper, ADP-ribosyl-N₃ was designed and synthesized for the first time. With ADP-ribosyl-N₃ as the key precursor, a divergent post-modification strategy was developed to prepare structurally diverse ADP-ribosylated compounds including novel nucleotides and peptides bearing ADP-ribosyl moieties.

Keywords: ADP-ribosylated compounds; divergent synthesis; nucleotides.

MeSH terms

ADP-Ribosylation*
Adenosine Diphosphate Ribose / chemistry*
Chemistry Techniques, Synthetic / methods*
Diphosphates / chemistry
Hydrophobic and Hydrophilic Interactions
Magnetic Resonance Spectroscopy / methods
Mass Spectrometry / methods
Molecular Structure
Nucleotides / chemical synthesis
Peptides / chemical synthesis

Substances

Diphosphates
Nucleotides
Peptides
Adenosine Diphosphate Ribose
diphosphoric acid