Issue 3, 2013
From the journal:

Chemical Communications

Oligonucleotidecyclization: the thiol-maleimide reaction revisited†

Albert Sánchez,a   Enrique Pedrosoa  and  Anna Grandas*a  

* Corresponding authors

a Departament de Química Orgànica and IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain
E-mail: anna.grandas@ub.edu
Fax: +34 933397878
Tel: +34 934021263

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.

Graphical abstract: Oligonucleotide cyclization: the thiol-maleimide reaction revisited

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Article information

DOI
https://doi.org/10.1039/C2CC35357A
Article type
Communication
Submitted
24 Jul 2012
Accepted
13 Nov 2012
First published
13 Nov 2012

Chem. Commun., 2013,49, 309-311

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Oligonucleotide cyclization: the thiol-maleimide reaction revisited

A. Sánchez, E. Pedroso and A. Grandas, Chem. Commun., 2013, 49, 309 DOI: 10.1039/C2CC35357A

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