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Synlett 2017; 28(08): 924-928
DOI: 10.1055/s-0036-1588689
letter
Georg Thieme Verlag Stuttgart · New York

Tuning the Properties of Penetrating Peptides by Oxime Conjugation

Marta Pazo
Singular Research Centre in Chemical Biology and Molecular Materials, (CIQUS), Organic Chemistry Department, University of Santiago de Compostela (USC), Santiago de Compostela, Spain   Email: javier.montenegro@usc.es
,
Héctor Fernández-Caro
Singular Research Centre in Chemical Biology and Molecular Materials, (CIQUS), Organic Chemistry Department, University of Santiago de Compostela (USC), Santiago de Compostela, Spain   Email: javier.montenegro@usc.es
,
Juan M. Priegue
Singular Research Centre in Chemical Biology and Molecular Materials, (CIQUS), Organic Chemistry Department, University of Santiago de Compostela (USC), Santiago de Compostela, Spain   Email: javier.montenegro@usc.es
,
Irene Lostalé-Seijo
Singular Research Centre in Chemical Biology and Molecular Materials, (CIQUS), Organic Chemistry Department, University of Santiago de Compostela (USC), Santiago de Compostela, Spain   Email: javier.montenegro@usc.es
,
Javier Montenegro*
Singular Research Centre in Chemical Biology and Molecular Materials, (CIQUS), Organic Chemistry Department, University of Santiago de Compostela (USC), Santiago de Compostela, Spain   Email: javier.montenegro@usc.es
› Author Affiliations
Further Information

Publication History

Received: 14 October 2016

Accepted after revision: 20 December 2016

Publication Date:
25 January 2017 (online)

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Abstract

We here describe the application of oxime bond formation between a peptide scaffold and different aldehydes to modify the transporting capabilities of penetrating peptides. We show that bonds such as oximes offer a great synthetic advantage for the modification of the properties of model penetrating peptides. We believe that this approach will allow the development of improved intracellular delivery vehicles.

Key words

peptide chemistry - penetrating peptides - supramolecular chemistry - membrane transport - solid-phase peptide synthesis

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588689.
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