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Nucleic Acids Research 2006 34(3):e24; doi:10.1093/nar/gnj020
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Published online 14 February 2006

© The Author 2006. Published by Oxford University Press. All rights reserved
The online version of this article has been published under an open access model. Users are entitled to use, reproduce, disseminate, or display the open access version of this article for non-commercial purposes provided that: the original authorship is properly and fully attributed; the Journal and Oxford University Press are attributed as the original place of publication with the correct citation details given; if an article is subsequently reproduced or disseminated not in its entirety but only in part or as a derivative work this must be clearly indicated. For commercial re-use, please contact journals.permissions{at}oxfordjournals.org

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Diels-Alder cycloadditions in water for the straightforward preparation of peptide–oligonucleotide conjugates

Vicente Marchán, Samuel Ortega, Daniel Pulido, Enrique Pedroso and Anna Grandas*

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

*To whom correspondence should be addressed. Tel: +34 93 402 12 63; Fax: +34 93 339 78 78; Email: anna.grandas{at}ub.edu

Received November 18, 2005. Revised December 16, 2005. Accepted January 19, 2006.

The Diels-Alder reaction between diene-modified oligonucleotides and maleimide-derivatized peptides afforded peptide–oligonucleotide conjugates with high purity and yield. Synthesis of the reagents was easily accomplished by on-column derivatization of the corresponding peptides and oligonucleotides. The cycloaddition reaction was carried out in mild conditions, in aqueous solution at 37°C. The speed of the reaction was found to vary depending on the size of the reagents, but it can be completed in 8–10 h by reacting the diene-oligonucleotide with a small excess of maleimide-peptide.

Correspondence may also be addressed to Vicente Marchán. Tel: +34 93 402 12 49; Fax: +34 93 339 78 78; Email: vmarchan{at}ub.edu


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