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Issue 47, 2019
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Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols

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Abstract

New open-chain and water-soluble hypervalent iodine reagents were synthesized and used for the transfer of fluoroalkyl groups to sulfur atoms of cysteine and cysteine-containing peptides under biocompatible conditions. Some of the reagents displayed excellent reactivity despite their limited stability in aqueous media. In reactions with a short cysteine-containing peptide, in addition to the expected S-fluoroalkylated product, a range of side-products were obtained. The amount of side-products depended on the conditions used (type of reagent, concentration, and pH). With highly activated hypervalent iodine reagents, a new reactive mode was observed – reaction with disulfides to form fluoroalkyl thiols.

Graphical abstract: Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols

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Supplementary files

Article information


Submitted
30 Sep 2019
Accepted
11 Nov 2019
First published
13 Nov 2019

Org. Biomol. Chem., 2019,17, 10097-10102
Article type
Paper

Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols

I. Klimánková, M. Hubálek, V. Matoušek and P. Beier, Org. Biomol. Chem., 2019, 17, 10097
DOI: 10.1039/C9OB02115A

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