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Accepted version

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2014-03-11

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/53528

Orthogonal protection of peptides and peptoids for cyclization by the thiol-ene reaction and conjugation

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http://dx.doi.org/10.1021/jo500427c

Abstract

Cyclic peptides and peptoids were prepared using the thiol-ene Michael-type reaction. The linear precursors were provided with additional functional groups allowing for subsequent conjugation: an orthogonally protected thiol, a protected maleimide, or an alkyne. The functional group for conjugation was placed either within the cycle or in an external position. The click reactions employed for conjugation with suitably derivatized nucleoside or oligonucleotides were either cycloadditions (Diels-Alder, Cu(I)-catalyzed azide-alkyne) or the same Michael-type reaction as for cyclization.

Subject

Pèptids, Àcids nucleics, Ciclització (Química), Aminoàcids, Proteïnes

Subject (English)

Peptides, Nucleic acids, Ring formation (Chemistry), Amino acids, Proteins

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

ELDUQUE BUSQUETS, Xavier, PEDROSO MULLER, Enrique and GRANDAS SAGARRA, Anna. Orthogonal protection of peptides and peptoids for cyclization by the thiol-ene reaction and conjugation. Journal of Organic Chemistry. 2014. Vol. 79, num. 7, pags. 2843-2853. ISSN 0022-3263. [consulted: 13 of June of 2026]. Available at: https://hdl.handle.net/2445/53528

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