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Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX
Stockholm University, Faculty of Science, Department of Organic Chemistry. Ecole Polytechnique Fédérale de Lausanne, Switzerland.
Number of Authors: 3
2016 (English)In: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 12, 745-749 p.Article in journal (Refereed) Published
Abstract [en]

The selective functionalization of peptides containing only natural amino acids is important for the modification of biomolecules. In particular, the installation of an alkyne as a useful handle for bioconjugation is highly attractive, but the use of a carbon linker is usually required. Herein, we report the gold-catalyzed direct alkynylation of tryptophan in peptides using the hypervalent iodine reagent TIPS-EBX (1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one). The reaction proceeded in 50-78% yield under mild conditions and could be applied to peptides containing other nucleophilic and aromatic amino acids, such as serine, phenylalanine or tyrosine.

Place, publisher, year, edition, pages
2016. Vol. 12, 745-749 p.
Keyword [en]
alkynes, C-H functionalization, gold catalysis, hypervalent iodine, peptides
National Category
Organic Chemistry
URN: urn:nbn:se:su:diva-130874DOI: 10.3762/bjoc.12.74ISI: 000374468200001OAI: diva2:934008
Available from: 2016-06-07 Created: 2016-06-07 Last updated: 2016-06-07Bibliographically approved

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Tolnai, Gergely L.
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