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Synthesis of Adenosine Diphosphate Ribose Histidine.

Bob van Puffelen1, Yang Lu2, Hugo Minnee1

  • 1Leiden Institute of Chemistry, Leiden University, 2333 CC Leiden, The Netherlands.

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|January 8, 2026
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Summary
This summary is machine-generated.

Adenosine diphosphate ribosylated histidine (His-ADPr) is a bacterial signaling molecule crucial for antiphage defense. Researchers synthesized His-ADPr and a triazole isostere to assess the stability of this important metabolite against ribosyl hydrolases.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Bacteriology

Background:

  • Adenosine diphosphate ribosylated histidine (His-ADPr) is a critical second messenger.
  • His-ADPr plays a vital role in bacterial immune systems, particularly in antiphage defense mechanisms.
  • The molecule features a unique ribosylation at the distal nitrogen of the histidine side chain in a β-fashion.

Purpose of the Study:

  • To synthesize the bacterial metabolite His-ADPr.
  • To synthesize a triazole isostere of His-ADPr.
  • To evaluate the stability of His-ADPr against relevant ribosyl hydrolases.

Main Methods:

  • Chemical synthesis of His-ADPr.
  • Chemical synthesis of the triazole isostere.
  • Enzymatic assays to assess stability against ribosyl hydrolases.

Main Results:

  • Successful synthesis of His-ADPr and its triazole isostere.
  • Characterization of the stability profile of His-ADPr.
  • Insights into the enzymatic degradation pathways of His-ADPr.

Conclusions:

  • His-ADPr is a synthetically accessible bacterial metabolite.
  • The stability of His-ADPr under enzymatic conditions was elucidated.
  • This research provides a foundation for understanding His-ADPr metabolism and function in bacterial defense.