Počet záznamů: 1
Visible-Light-Driven Fluoroalkylation of Tryptophan Residues in Peptides
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SYSNO ASEP 0540179 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Visible-Light-Driven Fluoroalkylation of Tryptophan Residues in Peptides Tvůrce(i) Rahimidashaghoul, Kheironnesae (UOCHB-X)
Klimánková, Iveta (UOCHB-X)
Hubálek, Martin (UOCHB-X) RID, ORCID
Matoušek, V. (CZ)
Filgas, Josef (UOCHB-X) ORCID
Slavíček, P. (CZ)
Slanina, Tomáš (UOCHB-X) ORCID, RID
Beier, Petr (UOCHB-X) RID, ORCIDZdroj.dok. ChemPhotoChem . - : Wiley - ISSN 2367-0932
Roč. 5, č. 1 (2021), s. 43-50Poč.str. 8 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova bioconjugation ; fluoroalkylation ; iodanes ; peptides ; radical reactions Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry CEP GA17-00598S GA ČR - Grantová agentura ČR GJ19-20467Y GA ČR - Grantová agentura ČR Způsob publikování Omezený přístup Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000572506800001 EID SCOPUS 85091459109 DOI 10.1002/cptc.202000214 Anotace 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. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2022 Elektronická adresa https://doi.org/10.1002/cptc.202000214
Počet záznamů: 1