Journal article

Solid-Phase-Based Synthesis of Ureidopyrimidinone-Peptide Conjugates for Supramolecular Biomaterials

Isja de Feijter, Olga JGM Goor, Simone IS Hendrikse, Marta Comellas-Aragones, Serge HM Sontjens, Sabrina Zaccaria, Peter PKH Fransen, Joris W Peeters, Lech-Gustav Milroy, Patricia YW Dankers

SYNLETT | GEORG THIEME VERLAG KG | Published : 2015

Abstract

Supramolecular polymers have shown to be powerful scaffolds for tissue engineering applications. Supramolecular biomaterials functionalized with ureidopyrimidinone (UPy) moieties, which dimerize via quadruple hydrogen-bond formation, are eminently suitable for this purpose. The conjugation of the UPy moiety to biologically active peptides ensures adequate integration into the supramolecular UPy polymer matrix. The structural complexity of UPy-peptide conjugates makes their synthesis challenging and until recently low yielding, thus restricted the access to structurally diverse derivatives. Here we report optimization studies of a convergent solid-phase based synthesis of UPy-modified peptide..

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University of Melbourne Researchers

Grants

Awarded by Ministry of Education, Culture and Science


Awarded by European Research Council


Awarded by Union's Seventh Framework Programme


Awarded by Marie Curie Actions


Funding Acknowledgements

We thank Ewelina Burakowska-Meise for initial experiments, and Jolanda J. H. Spiering, Maarten H. Bakker and Joost L. J. van Dongen for assistance with synthesis and analysis. Furthermore we gratefully acknowledge E. W. Meijer, Henk M. Janssen, and Maartje M. C. Bastings for scientific discussions. The research leading to these results has received funding from the Ministry of Education, Culture and Science (Gravity program 024.001.035), the Netherlands Organisation for Scientific Research (NWO), the European Research Council (FP7/2007-2013) ERC Grant Agreement number 308045, the Union's Seventh Framework Programme (FP/2007-2013) Grant Agreement number 310389, and Marie Curie Actions (VLPsiRNA-FP7-PEOPLE-2009-IOF-254069). This research forms part of the Project P3.01 BioKid of the research program of the BioMedical Materials institute, co-funded by the Dutch Ministry of Economic Affairs. The financial contribution of the Dutch Kidney Foundation is gratefully acknowledged.