4-Chloro-L-kynurenine as fluorescent amino acid in natural peptides.

Autor: Alferova VA; Gause Institute of New Antibiotics, Bolshaya Pirogovskaya 11, Moscow, 119021, Russia., Shuvalov MV; Gause Institute of New Antibiotics, Bolshaya Pirogovskaya 11, Moscow, 119021, Russia.; Department of Chemistry, Lomonosov Moscow State University, 1-3 Leninskie Gory, Moscow, 119992, Russia., Suchkova TA; Gause Institute of New Antibiotics, Bolshaya Pirogovskaya 11, Moscow, 119021, Russia.; Department of Chemistry, Lomonosov Moscow State University, 1-3 Leninskie Gory, Moscow, 119992, Russia., Proskurin GV; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow, 117997, Russia., Aparin IO; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow, 117997, Russia., Rogozhin EA; Gause Institute of New Antibiotics, Bolshaya Pirogovskaya 11, Moscow, 119021, Russia.; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow, 117997, Russia., Novikov RA; Engelhardt Institute of Molecular Biology, Vavilova 32, Moscow, 119991, Russia., Solyev PN; Engelhardt Institute of Molecular Biology, Vavilova 32, Moscow, 119991, Russia., Chistov AA; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow, 117997, Russia.; Orekhovich Research Institute of Biomedical Chemistry, Pogodinskaya 10, Moscow, 119121, Russia., Ustinov AV; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow, 117997, Russia., Tyurin AP; Gause Institute of New Antibiotics, Bolshaya Pirogovskaya 11, Moscow, 119021, Russia.; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow, 117997, Russia., Korshun VA; Gause Institute of New Antibiotics, Bolshaya Pirogovskaya 11, Moscow, 119021, Russia. v-korshun@yandex.ru.; Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, Moscow, 117997, Russia. v-korshun@yandex.ru.
Jazyk: angličtina
Zdroj: Amino acids [Amino Acids] 2018 Dec; Vol. 50 (12), pp. 1697-1705. Date of Electronic Publication: 2018 Sep 03.
DOI: 10.1007/s00726-018-2642-3
Abstrakt: 4-Chloro-L-kynurenine (3-(4-chloroanthraniloyl)-L-alanine, L-4-ClKyn), an amino acid known as a prospective antidepressant, was recently for the first time found in nature in the lipopeptide antibiotic taromycin. Here, we report another instance of its identification in a natural product: 4-chloro-L-kynurenine was isolated from acidic hydrolysis of a new complex peptide antibiotic INA-5812. L-4-ClKyn is a fluorescent compound responsible for the fluorescence of the above antibiotic. Whereas fluorescence of 4-chlorokynurenine was not reported before, we synthesized the racemic compound and studied its emission in various solvents. Next, we prepared conjugates of DL-4-ClKyn with two suitable energy acceptors, BODIPY FL and 3-(phenylethynyl)perylene (PEPe), and studied fluorescence of the derivatives. 4-Chloro-DL-kynurenine emission is not detected in both conjugates, thus evidencing effective energy transfer. However, BODIPY FL emission in the conjugate is substantially reduced, probably due to collisional or photoinduced charge-transfer-mediated quenching. The intrinsic fluorescence of L-4-ClKyn amino acid in antibiotics paves the way for spectral studies of their mode of action.
Databáze: MEDLINE
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