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Inverse electron-demand Diels-Alder bioconjugation using 7-oxanorbornenes as dienophiles Agramunt, Jordi Ginesi, Rebecca Pedroso Muller, Enrique Grandas Sagarra, Anna Solucions (Química) Pèptids Proteïnes Biopolímers Dissolvents Solution (Chemistry) Peptides Proteins Biopolymers Solvents Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, d-biotin, BODIPY, or N-acetyl-d-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37 °C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles. 2020-05-18T08:04:31Z 2021-04-22T05:10:20Z 2020-04-22 2020-05-18T08:04:31Z info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.0c00583 Journal of Organic Chemistry, 2020, vol. 85, num. 10, p. 6593-6604 https://doi.org/10.1021/acs.joc.0c00583 (c) American Chemical Society , 2020 info:eu-repo/semantics/openAccess American Chemical Society Articles publicats en revistes (Química Inorgànica i Orgànica)