title: Maleimide-dimethylfuran exo adducts: effective maleimide protection in the synthesis of oligonucleotide conjugates.
abstract: The reaction of maleimide-containing compounds with 2,5-dimethylfuran gives a mixture of exo and endo isomers from which the exo cycloadduct can be easily isolated taking advantage of its stability in concentrated aqueous ammonia. Bifunctional compounds incorporating a dimethylfuran-protected maleimide (exo adduct) have been attached to resin-linked oligonucleotide chains. Removal of protecting groups masking oligonucleotide functionalities followed by retro-Diels-Alder maleimide deprotection affords maleimido-oligonucleotides suitable for conjugation, as assessed by their reaction with different thiols.
authors.affiliation: Departament de Química Orgànica and IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain.
authors.forename: Albert
authors.initials: A
authors.lastname: Sánchez
authors.forename: Enrique
authors.initials: E
authors.lastname: Pedroso
authors.forename: Anna
authors.initials: A
authors.lastname: Grandas
mesh_terms: D005663:Furans / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D005663:Furans; D008301:Maleimides; D009841:Oligonucleotides; D013438:Sulfhydryl Compounds; C043592:maleimide; C037555:2,5-dimethylfuran