Details

Autor(en) / Beteiligte

• Alferova, Vera A.
• Shuvalov, Maxim V.
• Suchkova, Taisiya A.
• Proskurin, Gleb V.
• Aparin, Ilya O.
• Rogozhin, Eugene A.
• Novikov, Roman A.
• Solyev, Pavel N.
• Chistov, Alexey A.
• Ustinov, Alexey V.
• Tyurin, Anton P.
• Korshun, Vladimir A.

Titel

4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides

Ist Teil von

• Amino acids, 2018-12, Vol.50 (12), p.1697-1705

Ort / Verlag

Vienna: Springer Vienna

Erscheinungsjahr

2018

Quelle

MEDLINE

Beschreibungen/Notizen

• 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.