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The growing interest in ADP\u2010ribosylation necessitates straightforward and efficient synthetic methods for the preparation of ADP\u2010ribosylated peptides\/proteins. In this study, we report a facile reaction between nicotinamide adenine dinucleotide (NAD\n                    <jats:sup>+<\/jats:sup>\n                    ) and alcohols promoted by a combination of ionic liquids, yielding up to 94\u2009% with \u03b1\u2009:\u2009\u03b2 ratios ranging from 88\u2009:\u200912 to 99\u2009:\u20091 and a switchable configuration selectivity. This method significantly simplifies the production of ADP\u2010ribosylated peptides and proteins, enabling diverse applications. It allows detailed investigation of side\u2010chain structure\u2013activity relationships, facilitates two\u2010step clickable conjugation of ADP\u2010ribosyl groups to proteins, and, for the first time, enables non\u2010enzymatic synthesis of well\u2010defined ADP\u2010ribosylated peptides\/proteins from natural counterparts and NAD\n                    <jats:sup>+<\/jats:sup>\n                    .\n                  <\/jats:p>","DOI":"10.1002\/anie.202418321","type":"journal-article","created":{"date-parts":[[2025,1,6]],"date-time":"2025-01-06T03:15:36Z","timestamp":1736133336000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Chemical\n                    <i>O<\/i>\n                    \u2010ADP\u2010Ribosylations: Synthesis and Bioconjugation of ADPr\u2010Peptides\/Proteins from NAD\n                    <sup>+<\/sup>"],"prefix":"10.1002","volume":"64","author":[{"given":"Yanbo","family":"You","sequence":"first","affiliation":[{"name":"School of Chemistry and Chemical Engineering Henan Normal University  Xinxiang Henan 453007 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anlian","family":"Zhu","sequence":"additional","affiliation":[{"name":"Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals School of Chemistry and Chemical Engineering Key laboratory of Green Chemical Media and Reactions Ministry of Education Henan Normal University  Xinxiang Henan 453007 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dongshuang","family":"Fan","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Henan Normal University  Xinxiang Henan 453007 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