Visible-Light-Driven Fluoroalkylation of Tryptophan Residues in Peptides

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F21%3A43920929" target="_blank" >RIV/60461373:22340/21:43920929 - isvavai.cz</a>

Alternative codes found

RIV/60461373:22340/20:43920929 RIV/61388963:_____/21:00540179 RIV/00216208:11310/21:10439273

Result on the web

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cptc.202000214" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cptc.202000214</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cptc.202000214" target="_blank" >10.1002/cptc.202000214</a>

Result language

angličtina

Original language name

Visible-Light-Driven Fluoroalkylation of Tryptophan Residues in Peptides

Original language description

Trifluoromethylated and fluoroalkylated cyclic λ3-iodanes and their acyclic salts were used for visible light-driven fluoroalkylation of tryptophan and tryptophan-containing peptides in aqueous media. In comparison to previously reported fluoroalkylation using similar reagents and sodium ascorbate as reductant, the photochemical process did not require any additive or catalyst and was more selective for Trp versus other aromatic amino acids due to the gradual production of fluoroalkyl radicals over the whole irradiation period. However, in the presence of Cys residues, both methods were not selective and cysteine sulfhydryl groups were fluoroalkylated in side reactions. Spectroscopic and photochemical investigations as well as quantum chemical calculations provided insight into the reaction mechanism. The process was found to be photoinduced involving the formation of fluoroalkyl radical from the excited state of λ3-iodane. © 2020 Wiley-VCH GmbH

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10403 - Physical chemistry

Project

<a href="/en/project/GA20-15825S" target="_blank" >GA20-15825S: Towards Accurate Computational Spectroscopy: Merging Quantum Mechanics with Statistical Techniques</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2021

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

ChemPhotoChem

ISSN

2367-0932

e-ISSN

—

Volume of the periodical

5

Issue of the periodical within the volume

1

Country of publishing house

DE - GERMANY

Number of pages

9

Pages from-to

43-50

UT code for WoS article

000572506800001

EID of the result in the Scopus database

2-s2.0-85091459109