Oligonucleotide cyclization: the thiol-maleimide reaction revisited.

Albert Sánchez, Enrique Pedroso, Anna Grandas

Departament de Química Orgànica and IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain.

Chemical communications (Cambridge, England) 2013 Jan 11

filter terms:

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.

Citation

Albert Sánchez, Enrique Pedroso, Anna Grandas. Oligonucleotide cyclization: the thiol-maleimide reaction revisited. Chemical communications (Cambridge, England). 2013 Jan 11;49(3):309-11