Unexpected Coelenterazine Degradation Products of Beroe abyssicola Photoprotein Photoinactivation.

Autor: Burakova LP; Photobiology Laboratory, Institute of Biophysics SB RAS, Federal Research Center 'Krasnoyarsk Science Center SB RAS', Krasnoyarsk 660036, Russia., Lyakhovich MS; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Mineev KS; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Moscow Institute of Physics and Technology, Dolgoprudny 141701, Russia., Petushkov VN; Photobiology Laboratory, Institute of Biophysics SB RAS, Federal Research Center 'Krasnoyarsk Science Center SB RAS', Krasnoyarsk 660036, Russia., Zagitova RI; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Tsarkova AS; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Pirogov Russian National Research Medical University, 117997 Moscow, Russia., Kovalchuk SI; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia., Yampolsky IV; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Pirogov Russian National Research Medical University, 117997 Moscow, Russia., Vysotski ES; Photobiology Laboratory, Institute of Biophysics SB RAS, Federal Research Center 'Krasnoyarsk Science Center SB RAS', Krasnoyarsk 660036, Russia., Kaskova ZM; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, Moscow 117997, Russia.; Pirogov Russian National Research Medical University, 117997 Moscow, Russia.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2021 Sep 03; Vol. 23 (17), pp. 6846-6849. Date of Electronic Publication: 2021 Aug 20.
DOI: 10.1021/acs.orglett.1c02410
Abstrakt: Ca 2+ -regulated photoproteins of ctenophores lose bioluminescence activity when exposed to visible light. Little is known about the chemical nature of chromophore photoinactivation. Using a total synthesis strategy, we have established the structures of two unusual coelenterazine products, isolated from recombinant berovin of the ctenophore Beroe abyssicola , which are Z / E isomers. We propose that during light irradiation, these derivatives are formed from 2-hydroperoxycoelenterazine via the intermediate 8a-peroxide by a mechanism reminiscent of that previously described for the auto-oxidation of green-fluorescent-protein-like chromophores.
Databáze: MEDLINE
Externí odkaz: