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

被引:14
作者
Klimankova, Iveta [1 ]
Hubalek, Martin [1 ]
Matousek, Vaclav [2 ]
Beier, Petr [1 ]
机构
[1] Czech Acad Sci, Inst Organ Chem & Biochem, Flemingovo Namesti 2, Prague 16610 6, Czech Republic
[2] CF Plus Chem Sro, Karasek 1767-1, Brno 62100, Czech Republic
关键词
S-TRIFLUOROMETHYLATION; F-19; NMR; PROTEIN; PEPTIDES;
D O I
10.1039/c9ob02115a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:10097 / 10102
页数:6
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