{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T12:58:31Z","timestamp":1790945911352,"version":"4.1.0"},"reference-count":36,"publisher":"American Chemical Society (ACS)","issue":"39","license":[{"start":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T00:00:00Z","timestamp":1789689600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T00:00:00Z","timestamp":1789689600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T00:00:00Z","timestamp":1789689600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100011447","name":"Science and Technology Department of Henan Province","doi-asserted-by":"publisher","award":["242300421005"],"award-info":[{"award-number":["242300421005"]}],"id":[{"id":"10.13039\/501100011447","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22473040"],"award-info":[{"award-number":["22473040"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["U23A20106"],"award-info":[{"award-number":["U23A20106"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Nicotinic acid adenine dinucleotide phosphate (NAADP+) and related NAD(P)+ analogues are important tools for calcium signaling, redox biology, and chemical biology. Their preparation, however, remains constrained by lengthy dinucleotide synthesis and enzyme-dependent base exchange. Here we describe a biomimetic chemical base-exchange reaction that converts native NAD+ or NADP+ directly into NAAD+, NAADP+, and modified pyridine nucleotide analogues. Fe(III) promotes substitution of the nicotinamide unit through synergistic activation of the cationic C\u2013N glycosidic bond.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03255","type":"journal-article","created":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T23:01:24Z","timestamp":1789772484000},"page":"12212-12217","source":"Crossref","is-referenced-by-count":0,"title":["Biomimetic Base-Exchange\nReaction for Late-Stage Synthesis\nof Stereodivergent NAADP+ and NAD(P)+ Derivatives"],"prefix":"10.1021","volume":"28","author":[{"given":"Shaoying","family":"Wang","sequence":"first","affiliation":[{"name":"Henan Normal University , , , ,","place":["Xinxiang, Henan, China, 453007"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanbo","family":"You","sequence":"additional","affiliation":[{"name":"The First Affiliated Hospital of Henan University of Science and Technology , , , ,","place":["Luoyang, Henan, China, 471000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anlian","family":"Zhu","sequence":"additional","affiliation":[{"name":"Henan Normal University , , , ,","place":["Xinxiang, Henan, China, 453007"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4722-3637","authenticated-orcid":true,"given":"Lingjun","family":"Li","sequence":"additional","affiliation":[{"name":"Henan Normal University , , , ,","place":["Xinxiang, Henan, China, 453007"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,18]]},"reference":[{"key":"2026100208363920800_cit1","doi-asserted-by":"publisher","first-page":"1208","DOI":"10.1126\/science.aac4854","article-title":"NAD+ in aging, metabolism, and neurodegeneration","volume":"350","author":"Verdin","year":"2015","journal-title":"Science"},{"key":"2026100208363920800_cit2","doi-asserted-by":"publisher","first-page":"227","DOI":"10.1038\/s41392-020-00311-7","article-title":"NAD+ metabolism: pathophysiologic\nmechanisms and therapeutic potential","volume":"5","author":"Xie","year":"2020","journal-title":"Signal\nTransduction Targeted Ther."},{"key":"2026100208363920800_cit3","doi-asserted-by":"publisher","first-page":"26","DOI":"10.1038\/s44324-025-00067-0","article-title":"The role of\nNAD+ metabolism and its modulation of mitochondria in aging\nand disease","volume":"3","author":"Yusri","year":"2025","journal-title":"npj Metab. Health Dis."},{"key":"2026100208363920800_cit4","doi-asserted-by":"publisher","first-page":"307","DOI":"10.1038\/370307a0","article-title":"Cyclic\nADP ribose activation of the ryanodine receptor is mediated by calmodulin","volume":"370","author":"Lee","year":"1994","journal-title":"Nature"},{"key":"2026100208363920800_cit5","doi-asserted-by":"publisher","first-page":"70","DOI":"10.1038\/18024","article-title":"Regulation of calcium signalling\nin T lymphocytes by the second messenger cyclic ADP-ribose","volume":"398","author":"Guse","year":"1999","journal-title":"Nature"},{"key":"2026100208363920800_cit6","doi-asserted-by":"publisher","first-page":"119","DOI":"10.1038\/s41580-020-00313-x","article-title":"NAD+ metabolism\nand its roles in cellular processes during ageing","volume":"22","author":"Covarrubias","year":"2021","journal-title":"Nat. Rev. Mol. Cell Biol."},{"key":"2026100208363920800_cit7","doi-asserted-by":"publisher","first-page":"1092","DOI":"10.1021\/acs.chemrev.7b00122","article-title":"ADP-ribosylation,\na multifaceted posttranslational\nmodification involved in the control of cell physiology in health\nand disease","volume":"118","author":"Lu\u0308scher","year":"2018","journal-title":"Chem. Rev."},{"key":"2026100208363920800_cit8","doi-asserted-by":"publisher","first-page":"mr1","DOI":"10.1126\/scisignal.257mr1","article-title":"Emerging roles\nof NAD+ and its metabolites in cell signaling","volume":"2","author":"Koch-Nolte","year":"2009","journal-title":"Sci. Signaling"},{"key":"2026100208363920800_cit9","doi-asserted-by":"publisher","first-page":"2823","DOI":"10.1016\/S0021-9258(18)67903-7","article-title":"Substituted Nicotinamide Analogues of Nicotinamide\nAdenine Dinucleotide","volume":"238","author":"Walter","year":"1963","journal-title":"J. Biol. Chem."},{"key":"2026100208363920800_cit10","doi-asserted-by":"publisher","first-page":"1133","DOI":"10.1152\/physrev.1997.77.4.1133","article-title":"Mechanisms\nof calcium signaling by cyclic ADP-ribose and NAADP","volume":"77","author":"Lee","year":"1997","journal-title":"Physiol. Rev."},{"key":"2026100208363920800_cit11","doi-asserted-by":"publisher","first-page":"596","DOI":"10.1038\/nature08030","article-title":"NAADP mobilizes calcium from acidic\norganelles through two-pore channels","volume":"459","author":"Calcraft","year":"2009","journal-title":"Nature"},{"key":"2026100208363920800_cit12","doi-asserted-by":"publisher","first-page":"31633","DOI":"10.1074\/jbc.R112.349464","article-title":"Cyclic\nADP-ribose and nicotinic acid adenine dinucleotide phosphate (NAADP)\nas messengers for calcium mobilization","volume":"287","author":"Lee","year":"2012","journal-title":"J. Biol.\nChem."},{"key":"2026100208363920800_cit13","doi-asserted-by":"publisher","first-page":"74","DOI":"10.1038\/18032","article-title":"Coordination of agonist-induced Ca2+-signalling patterns by NAADP in pancreatic acinar cells","volume":"398","author":"Cancela","year":"1999","journal-title":"Nature"},{"key":"2026100208363920800_cit14","doi-asserted-by":"publisher","first-page":"R186","DOI":"10.1016\/S0960-9822(03)00120-9","article-title":"Calcium\nSignaling: NAADP Ascends as a New Messenger","volume":"13","author":"Lee","year":"2003","journal-title":"Curr. Biol."},{"key":"2026100208363920800_cit15","doi-asserted-by":"publisher","first-page":"703326","DOI":"10.3389\/fimmu.2021.703326","article-title":"NAADP: from discovery to mechanism","volume":"12","author":"Walseth","year":"2021","journal-title":"Front. Immunol."},{"key":"2026100208363920800_cit16","doi-asserted-by":"publisher","first-page":"7599","DOI":"10.1021\/jm1007209","article-title":"Nicotinic acid adenine\ndinucleotide phosphate analogues containing substituted nicotinic\nacid: effect of modification on Ca2+ release","volume":"53","author":"Jain","year":"2010","journal-title":"J. Med. Chem."},{"key":"2026100208363920800_cit17","doi-asserted-by":"publisher","first-page":"3593","DOI":"10.1021\/acs.jmedchem.5b00279","article-title":"Nicotinic acid adenine\ndinucleotide phosphate analogues substituted on the nicotinic acid\nand adenine ribosides. Effects on receptormediated Ca2+ release","volume":"58","author":"Trabbic","year":"2015","journal-title":"J. Med. Chem."},{"key":"2026100208363920800_cit18","doi-asserted-by":"publisher","first-page":"3321","DOI":"10.1021\/acssynbio.5c00473","article-title":"Engineering Noncanonical\nCofactors To Expand Cellular Functions","volume":"14","author":"Lim","year":"2025","journal-title":"ACS\nSynth. Biol."},{"key":"2026100208363920800_cit19","doi-asserted-by":"publisher","first-page":"1842","DOI":"10.1021\/acschembio.4c00425","article-title":"Diazirine-AIOC-NAADP,\na Clickable-Photoactive NAADP Analog for Sea Urchin NAADP Binding\nProteins","volume":"19","author":"Zhang","year":"2024","journal-title":"ACS Chem. Biol."},{"key":"2026100208363920800_cit20","doi-asserted-by":"publisher","first-page":"102060","DOI":"10.1016\/j.ceca.2019.102060","article-title":"The synthesis\nand characterization of a clickable-photoactive\nNAADP analog active in human cells","volume":"83","author":"Asfaha","year":"2019","journal-title":"Cell Calcium"},{"key":"2026100208363920800_cit21","doi-asserted-by":"publisher","first-page":"2296","DOI":"10.1074\/jbc.M111.305813","article-title":"Photoaffinity\nLabeling of Nicotinic Acid Adenine Dinucleotide Phosphate (NAADP)\nTargets in Mammalian Cells*\u25c6","volume":"287","author":"Lin-Moshier","year":"2012","journal-title":"J. Biol.\nChem."},{"key":"2026100208363920800_cit22","doi-asserted-by":"publisher","first-page":"822","DOI":"10.1038\/s41929-025-01390-x","article-title":"An NAD+ analogue enables\nassembly of structurally diverse artificial photoenzymes for enantiodivergent\n[2 + 2] cycloadditions","volume":"8","author":"Du","year":"2025","journal-title":"Nat. Catal."},{"key":"2026100208363920800_cit23","doi-asserted-by":"publisher","first-page":"8008","DOI":"10.1038\/s41467-024-52024-y","article-title":"MASTER-NAADP:\na membrane permeable precursor of the Ca2+ mobilizing second\nmessenger NAADP","volume":"15","author":"Krukenberg","year":"2024","journal-title":"Nat. Commun."},{"key":"2026100208363920800_cit24","doi-asserted-by":"publisher","first-page":"93","DOI":"10.1016\/j.ceca.2013.12.004","article-title":"Activity of Nicotinic Acid Substituted\nNicotinic Acid Adenine Dinucleotide Phosphate (NAADP) Analogs in a\nHuman Cell Line: Difference in Specificity between Human and Sea Urchin\nNAADP Receptors","volume":"55","author":"Ali","year":"2014","journal-title":"Cell Calcium"},{"key":"2026100208363920800_cit25","doi-asserted-by":"publisher","first-page":"9035","DOI":"10.1021\/bi970263e","article-title":"Caged NADP and\nNAD. Synthesis and Characterization of Functionally Distinct Caged\nCompounds","volume":"36","author":"Cohen","year":"1997","journal-title":"Biochemistry"},{"key":"2026100208363920800_cit26","doi-asserted-by":"publisher","first-page":"pdb.prot076943","DOI":"10.1101\/pdb.prot076943","article-title":"Synthesis\nof Caged NAADP","volume":"2014","author":"Galione","year":"2014","journal-title":"Cold Spring Harbor. Protoc."},{"key":"2026100208363920800_cit27","doi-asserted-by":"publisher","first-page":"4637","DOI":"10.1002\/anie.200460054","article-title":"Chemical synthesis\nof the second messenger nicotinic\nacid adenine dinucleotide phosphate by total synthesis of nicotinamide\nadenine dinucleotide phosphate","volume":"43","author":"Dowden","year":"2004","journal-title":"Angew. Chem."},{"key":"2026100208363920800_cit28","doi-asserted-by":"publisher","first-page":"8337","DOI":"10.1039\/C8SC03899F","article-title":"Facile chemoenzymatic\nsynthesis of a novel stable mimic of NAD+","volume":"9","author":"Dai","year":"2018","journal-title":"Chem. Sci."},{"key":"2026100208363920800_cit29","doi-asserted-by":"publisher","first-page":"30327","DOI":"10.1074\/jbc.270.51.30327","article-title":"ADP-ribosyl\ncyclase and CD38 catalyze the synthesis of a calcium-mobilizing metabolite\nfrom NADP+","volume":"270","author":"Aarhus","year":"1995","journal-title":"J. Biol. Chem."},{"key":"2026100208363920800_cit30","doi-asserted-by":"publisher","first-page":"3971","DOI":"10.1021\/jo9917846","article-title":"Enzymatic\nsynthesis of caged NADP\ncofactors: aqueous NADP photorelease and optical properties","volume":"65","author":"Salerno","year":"2000","journal-title":"J. Org. Chem."},{"key":"2026100208363920800_cit31","doi-asserted-by":"publisher","first-page":"10787","DOI":"10.1021\/ja00102a055","article-title":"Cyclic ADP-Ribose via Stereoselective\nCyclization of \u03b2-NAD+","volume":"116","author":"Yamada","year":"1994","journal-title":"J. Am.\nChem. Soc."},{"key":"2026100208363920800_cit32","doi-asserted-by":"publisher","first-page":"5600","DOI":"10.1038\/s41467-020-19409-1","article-title":"Biomimetic \u03b1-selective ribosylation enables two-step modular\nsynthesis of biologically important ADP-ribosylated peptides","volume":"11","author":"Zhu","year":"2020","journal-title":"Nat. Commun."},{"key":"2026100208363920800_cit33","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202418321","article-title":"Chemical O-ADP-Ribosylations:\nSynthesis and Bioconjugation of ADPr-Peptides\/Proteins from NAD+","volume":"137","author":"You","year":"2025","journal-title":"Angew. Chem."},{"key":"2026100208363920800_cit34","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.202500731","article-title":"Enzymatic\nand Chemical Synthesis for ADP-Ribosylation\nUsing NAD+ as Building Blocks: New Concerns in Reaction\nDiscovery and Design","volume":"27","author":"Liu","year":"2026","journal-title":"ChemBioChem."},{"key":"2026100208363920800_cit35","doi-asserted-by":"publisher","first-page":"8242","DOI":"10.1021\/acs.chemrev.8b00083","article-title":"The experimental evidence in support\nof glycosylation mechanisms\nat the SN1-SN2 interface","volume":"118","author":"Adero","year":"2018","journal-title":"Chem. Rev."},{"key":"2026100208363920800_cit36","doi-asserted-by":"publisher","first-page":"2298","DOI":"10.1021\/ic001042r","article-title":"Ionic liquids based\non FeCl3 and FeCl2. Raman scattering and ab initio calculations","volume":"40","author":"Sitze","year":"2001","journal-title":"Inorg. Chem."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c03255","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/39\/12212\/68562654\/acs.orglett.6c03255.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/39\/12212\/68562654\/acs.orglett.6c03255.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T12:50:24Z","timestamp":1790945424000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/39\/12212\/5433193\/Biomimetic-Base-Exchange-Reaction-for-Late-Stage"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,18]]},"references-count":36,"journal-issue":{"issue":"39","published-online":{"date-parts":[[2026,9,18]]},"published-print":{"date-parts":[[2026,10,2]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c03255","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,18]]}}}