Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX
2016 ◽
Vol 12
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pp. 745-749
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Keyword(s):
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.
2014 ◽
Vol 59
(6)
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pp. 581-588
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2016 ◽
Vol 20
(11)
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pp. 1232-1242
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1982 ◽
Vol 47
(1)
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pp. 210-216
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