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Herein, simple and one\u2010pot synthetic procedures have been implemented for producing a library of DNA nucleobase derivatives endowed with reactive functional groups for bioconjugation and cross\u2010linking strategies with other (bio)molecules. Purine and pyrimidine molecules have been regioselectively N\u2212H functionalized either via <jats:italic>N<\/jats:italic>\u2010alkylation, <jats:italic>N<\/jats:italic>\u2010allylation, <jats:italic>N<\/jats:italic>\u2010propargylation or Michael\u2010type reactions and structurally characterized. The influence of the reaction conditions was assessed and discussed. The in\u2005vitro biocompatibility of the native and nucleobase derivatives was evaluated by culturing them with human fibroblasts, revealing their cytocompatibility. The library of nucleobase derivatives holds great promise for being coupled to different biomolecules, including biopolymeric materials, lipids, and peptides, thus potentially leading to modular supramolecular nanobiomaterials for biomedicine.<\/jats:p>","DOI":"10.1002\/ejoc.202100786","type":"journal-article","created":{"date-parts":[[2021,7,26]],"date-time":"2021-07-26T10:04:27Z","timestamp":1627293867000},"page":"4423-4433","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Customizable and Regioselective One\u2010Pot N\u2212H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications"],"prefix":"10.1002","volume":"2021","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3508-9135","authenticated-orcid":false,"given":"Djenisa H. 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