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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 47期

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

页码：10097 / 10102

页数：6

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