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Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols
I. Klimánková, M. Hubálek, V. Matoušek, P. Beier,
Jazyk angličtina Země Velká Británie
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
31754683
DOI
10.1039/c9ob02115a
Knihovny.cz E-zdroje
- MeSH
- alkylace MeSH
- fluorované uhlovodíky chemická syntéza chemie MeSH
- indikátory a reagencie chemická syntéza chemie MeSH
- jod chemie MeSH
- molekulární struktura MeSH
- rozpustnost MeSH
- sulfhydrylové sloučeniny chemie MeSH
- voda chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
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.
Citace poskytuje Crossref.org
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