title: Oligonucleotide cyclization: the thiol-maleimide reaction revisited.
abstract: A novel method to synthesize cyclic oligonucleotides (5- to 26-mer) using the thiol-maleimide reaction is described. The target molecules were obtained after subsequent removal of thiol and maleimide protecting groups from 5'-maleimido-3'-thiol-derivatized linear precursors. Retro-Diels-Alder conditions deprotecting the maleimide simultaneously promoted cyclization cleanly and in high yield.
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: D003500:Cyclization; D061565:Cycloaddition Reaction; D008301:Maleimides / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D010084:Oxidation-Reduction; D013388:Succinimides / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D008301:Maleimides; D009841:Oligonucleotides; D013388:Succinimides; D013438:Sulfhydryl Compounds; C032620:succinimide; C043592:maleimide