化学
色氨酸
试剂
激进的
半胱氨酸
光化学
水溶液
催化作用
氨基酸
有机化学
组合化学
生物化学
酶
作者
Kheironnesae Rahimidashaghoul,Iveta Klimánková,Martin Hubálek,Václav Matoušek,Josef Filgas,Petr Slavı́ček,Tomáš Slanina,Petr Beier
出处
期刊:ChemPhotoChem
[Wiley]
日期:2020-09-25
卷期号:5 (1): 43-50
被引量:13
标识
DOI:10.1002/cptc.202000214
摘要
Abstract Trifluoromethylated and fluoroalkylated cyclic λ 3 ‐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 λ 3 ‐iodane.
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