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. 2026 Jan 23;28(3):917-922.
doi: 10.1021/acs.orglett.5c04626. Epub 2026 Jan 8.

Synthesis of Adenosine Diphosphate Ribose Histidine

Bob van Puffelen  1 , Yang Lu  2 , Hugo Minnee  1 , Marion Schuller  2 , Gijsbert A van der Marel  1 , Ivan Ahel  2 , Jeroen D C Codée  1 , Dmitri V Filippov  1
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Synthesis of Adenosine Diphosphate Ribose Histidine

Bob van Puffelen et al. Org Lett. .

Abstract

Adenosine diphosphate ribosylated histidine (His-ADPr) is a vital signaling molecule for the bacterial immune system, the antiphage system in particular. In this unique second messenger molecule, the distal nitrogen of the histidine side chain is ribosylated in a β fashion. Here, we describe the synthesis of this bacterial metabolite and its triazole isostere and evaluate the stability of His-ADPr to relevant ribosyl hydrolases.

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