Abstract
The synthesis of molecular conjugates through chemoselective ligations represents a very convenient strategy to prepare complex macromolecules with diverse functional elements. Herein, we describe chemical methods based on the preparation of chemoselectively addressable peptides allowing successive oxime ligations and/or alkyne–azide cycloaddition (“click”) reactions of various biomolecules. This modular synthetic approach can be applied to a broad range of purposes.
Key words
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Dawson, P. E. and Kent S. B. H. (2000) Synthesis of native proteins by chemical ligation. Annu. Rev. Biochem. 69, 923–960.
Hang, H. C. and Bertozzi, C. R. (2001) Chemoselective approaches to glycoprotein assembly. Acc. Chem. Res. 34, 727–736.
Carrico, I. S. (2008) Chemoselective modification of proteins: hitting the target. Chem. Soc. Rev. 37, 1423–1431.
Venkatesan, N. and Kim, B. H. (2006) Peptide conjugates of oligonucleotides: synthesis and applications. Chem. Rev., 106, 3712–3761.
Peri, F. and Nicotra, F. (2004) Chemoselective ligation in glycochemistry. Chem. Commun., 623–627.
Verez-Bencomo, V., Fernández-Santana, V., Hardy, E., Toledo, M. E., Rodríguez, M. C., Heynngnezz, L., Rodriguez, A., Baly, A., Herrera, L., Izquierdo, M., Villar, A., Valdés, Y., Cosme, K., Deler, M. L., Montane, M., Garcia, E., Ramos, A., Aguilar, A., Medina, E., Toraño, G., Sosa, I., Hernandez, I., Martínez, R., Muzachio, A., Carmenates, A., Costa, L., Cardoso, F., Campa, C., Diaz, M. and Roy, R. (2004) A synthetic conjugate polysaccharide vaccine against haemophilus influenzae type b. Science 305, 522–525.
Zeng, W., Jackson, D. C., Murray, J., Rose, K. and Brown, L. E. (2000) Vaccine 18, 1031–1039.
Rose, K. (1994) Facile synthesis of homogeneous artificial proteins. J. Am. Chem. Soc. 116, 30–33.
Canne, L. E., Ferré-D’Amare, A. R., Burley, S. K. and Kent S. B. H. (1995) Total chemical synthesis of a unique transcription factor-related protein: cMyc-Max. J. Am. Chem. Soc. 117, 2998–3007.
Naicker, K. P., Li, H., Heredia, A., Song H. and Wang, L.-X. (2004) Design and synthesis of αGal-conjugated peptide T20 as novel antiviral agent for HIV-immunotargeting. Org. Biomol. Chem. 2, 660–664.
Henry, M. D., Wen, S., Silva, M. D., Chandra, S., Milton, M. and Worland, P. J. (2004) A prostate-specific membrane antigen-targeted monoclonal antibody–chemotherapeutic conjugate designed for the treatment of prostate cancer. Cancer Res. 64, 7995–8001.
Garanger, E. Boturyn, D.; Renaudet, O. Defrancq, E. and Dumy, P. (2006) Chemoselectively addressable template: a valuable tool for the engineering of molecular conjugates. J. Org. Chem. 71, 2402–2410.
Renaudet, O., Boturyn, D. and Dumy, P. (2009) Biomolecular assembly by iterative oxime ligations. Bioorg. Med. Chem. Lett. 19, 3880–3883.
Tørnoe, C. W., Christensen, C. and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057–3064.
Rostovtsev, V. V., Green, L. G., Fokin, V. V. and Sharpless, K. B. (2002) A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes. Angew. Chem. Int. Ed. 41, 2596–2599.
Angell, Y. L. and Burgess, K. (2007) Peptidomimetics via copper-catalyzed azide–alkyne cycloadditions. Chem. Soc. Rev. 36, 1674–1689.
Galibert, M., Dumy, P. and Boturyn, D. (2009) One-pot approach to well-defined biomolecular assemblies via orthogonal chemoselective ligations. Angew. Chem. Int. Ed. 48, 2576–2579.
Duléry, V., Renaudet, O. and Dumy, P. (2007) Ethoxyethylidene protecting group prevents N-overacylation in aminooxy peptide synthesis. Tetrahedron 63, 11952–11958.
Foillard, S., Olsten Rasmussen, M., Razkin, J., Boturyn, D. and Dumy, P. (2008) 1-ethoxyethylidene, a new group for the stepwise spps of aminooxyacetic acid-containing peptides. J. Org. Chem. 73, 983–991.
Renaudet, O. and Dumy, P. (2006) On-bead synthesis and binding assay of chemoselectively template-assembled multivalent neoglycopeptides. Org. Biomol. Chem. 4, 2628–2636.
Renaudet, O., Křenek, K., Bossu, I., Dumy, P., Kádek, A., Adámek, D., Vaněk, O., Kavan, D., Gažák, R., Šulc, M., Bezouška, K. and Křen, V. (2010) synthesis of multivalent glycoconjugates containing the immunoactive LELTE peptide: Effect of Glycosylation on cellular activation and natural killing by human peripheral blood mononuclear cells. J. Am. Chem. Soc. 132, 6800–6808.
Acknowledgements
We thank the Université Joseph Fourier (UJF-Grenoble), the Centre National de la Recherche Scientifique (CNRS), and the NanoBio program (Grenoble) for providing support for this work.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2011 Springer Science+Business Media, LLC
About this protocol
Cite this protocol
Galibert, M., Renaudet, O., Boturyn, D., Dumy, P. (2011). Preparation of Peptide and Other Biomolecular Conjugates Through Chemoselective Ligations. In: Mark, S. (eds) Bioconjugation Protocols. Methods in Molecular Biology, vol 751. Humana Press. https://doi.org/10.1007/978-1-61779-151-2_6
Download citation
DOI: https://doi.org/10.1007/978-1-61779-151-2_6
Published:
Publisher Name: Humana Press
Print ISBN: 978-1-61779-150-5
Online ISBN: 978-1-61779-151-2
eBook Packages: Springer Protocols