Irreversible Cysteine-Selective Protein Labeling Employing Modular Electrophilic Tetrafluoroethylation Reagents
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00475804" target="_blank" >RIV/61388963:_____/17:00475804 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/chem.201700607" target="_blank" >http://dx.doi.org/10.1002/chem.201700607</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201700607" target="_blank" >10.1002/chem.201700607</a>
Alternative languages
Result language
angličtina
Original language name
Irreversible Cysteine-Selective Protein Labeling Employing Modular Electrophilic Tetrafluoroethylation Reagents
Original language description
Fluoroalkylation reagents based on hypervalent iodine are widely used to transfer fluoroalkyl moieties to various nucleophiles. However, the transferred groups have so far been limited to simple structural motifs. We herein report a reagent featuring a secondary amine that can be converted to amide, sulfonamide, and tertiary amine derivatives in one step. The resulting reagents bear manifold functional groups, many of which would not be compatible with the original synthetic pathway. Exploiting this structural versatility and the known high reactivity toward thiols, the new-generation reagents were used in bioconjugation with an artificial retro-aldolase, containing an exposed cysteine and a reactive catalytic lysine. Whereas commercial reagents based on maleimide and iodoacetamide labeled both sites, the iodanes exclusively modified the cysteine residue. The study thus demonstrates that modular fluoroalkylation reagents can be used as tools for cysteine-selective bioconjugation.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA17-00598S" target="_blank" >GA17-00598S: Development of fluoroalkylated hypervalent iodine reagents for thiol bioconjugations</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
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Volume of the periodical
23
Issue of the periodical within the volume
27
Country of publishing house
DE - GERMANY
Number of pages
5
Pages from-to
6490-6494
UT code for WoS article
000401160100003
EID of the result in the Scopus database
2-s2.0-85014222028