Synthesis of methylsulfanyl analogs of Kaede protein chromophore
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SHORT COMMUNICATION
Synthesis of methylsulfanyl analogs of Kaede protein chromophore Elvira R. Zaitseva1,2, Alexander Yu. Smirnov2*, Sofya I. Shcerbinina2, Vlada V. Zasedateleva2, Konstantin S. Mineev2, Mikhail S. Baranov2,3 1
D. Mendeleyev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047, Russia 2 Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia; е-mail: [email protected] 3 Pirogov Russian National Research Medical University, 1 Ostrovitianova St., Moscow 117997, Russia Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(3), 399–402
Submitted January 2, 2020 Accepted February 18, 2020
5-Arylidene-1-methyl-2-[2-(methylsulfanyl)-2-phenylethenyl]-1H-imidazol-5(4H)-ones were synthesized as a result of the reaction of 5-arylidene-1-methyl-2-(methylsulfanyl)-1H-imidazol-5(4H)-ones with terminal acetylenes in the presence of a palladium catalyst and copper iodide. This reaction presents a rare example of the formation of a compound with a methylsulfanylethenyl group. A study of the optical properties of the obtained compounds showed that they are characterized by a significant bathochromic shift of spectral maxima in comparison with similar derivatives of the GFP chromophore. Keywords: acetylenes, imidazolones, Kaede protein, chromophores, fluorogens, GFP chromophore.
5-Arylidene-2-alkylsulfanylimidazolones 2 are readily available stable reagents.11 They are structurally similar to the GFP chromophore and were previously used in the synthesis of its derivatives by arylation12 using metal complex catalysis. The aim of this work was to study the reactions of 5-arylidene-2-methylsulfanylimidazolones 2 with terminal acetylenes. As a result of our experiments, it turned out that the reaction of 5-arylidene-2-methylsulfanylimidazolones 2, obtained from 5-arylidene-2-thiooxoimidazolidinones 1, with acetylenes resulted in the formation of methylsulfanyl compounds 3 (Scheme 1). Moreover, in all cases, no appreciable amounts of acetylene derivative were found in the reaction mixture. Thus, the reaction we have proposed is not only a novel example of the synthesis of the Kaede protein chromophore derivatives, but also a rare example of the creation of a methylsulfanylethenyl group in a molecule. Moreover, we have shown that not only terminal arylacetylenes but also alkylacetylenes can be used in this
One of the most important modern methods for studying intracellular processes is fluorescence microscopy based on the use of fluorescent dyes. Among them, benzylideneimidazolones, analogs of the chromophore of green fluorescent protein (GFP), occupy an important place.1 These compounds are widely used due to the great variability of their optical properties, low toxicity, and synthetic availability.2,3 One of the subclasses of this group of dyes is the Kaede protein chromophore analogs, which are characterized by a significant bathochromic shift of spectral maxima compared to the original derivatives of th
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