Amino Acids, volume 50, issue 12, pages 1697-1705
4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides
Alferova Vera A
1
,
Shuvalov Maxim V
1, 2
,
Suchkova Taisiya A
1, 2
,
Proskurin Gleb V
3
,
Aparin Ilya O
3
,
Rogozhin Eugene A.
1, 3
,
Novikov Roman G.
4
,
Solyev Pavel N.
4
,
Chistov Alexey A
3, 5
,
Ustinov Alexey V
3
,
Tyurin Anton P
1, 3
,
Korshun Vladimir A.
1, 3
Publication type: Journal Article
Publication date: 2018-09-03
Journal:
Amino Acids
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor: 3.5
ISSN: 09394451, 14382199
Organic Chemistry
Biochemistry
Clinical Biochemistry
Abstract
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.
Citations by journals
|
1
2
|
|
|
Angewandte Chemie - International Edition
|
Angewandte Chemie - International Edition
2 publications, 25%
|
|
Angewandte Chemie
|
Angewandte Chemie
2 publications, 25%
|
|
Frontiers in Microbiology
|
Frontiers in Microbiology
1 publication, 12.5%
|
|
Tetrahedron Letters
|
Tetrahedron Letters
1 publication, 12.5%
|
|
Ageing Research Reviews
|
Ageing Research Reviews
1 publication, 12.5%
|
|
Expert Opinion on Investigational Drugs
|
Expert Opinion on Investigational Drugs
1 publication, 12.5%
|
|
1
2
|
Citations by publishers
|
1
2
3
4
|
|
|
Wiley
|
Wiley
4 publications, 50%
|
|
Elsevier
|
Elsevier
2 publications, 25%
|
|
Frontiers Media S.A.
|
Frontiers Media S.A.
1 publication, 12.5%
|
|
Taylor & Francis
|
Taylor & Francis
1 publication, 12.5%
|
|
1
2
3
4
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2019,2020,2021,2022,2023],"ids":[0,0,0,0,0],"codes":[0,0,0,0,0],"imageUrls":["","","","",""],"datasets":[{"label":"Citations number","data":[3,2,2,0,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["37.5","25","25",0,"12.5"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Angewandte Chemie - International Edition","Angewandte Chemie","Frontiers in Microbiology","Tetrahedron Letters","Ageing Research Reviews","Expert Opinion on Investigational Drugs"],"ids":[19215,25450,24403,6133,5462,1879],"codes":[0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp"],"datasets":[{"label":"","data":[2,2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[25,25,12.5,12.5,12.5,12.5],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","Elsevier","Frontiers Media S.A.","Taylor & Francis"],"ids":[11,17,208,18],"codes":[0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/4QWA67eqfcfyOiA8Wk7YnqroHFqQbTsmDJUYTCTg_medium.webp","\/storage\/images\/resized\/5YZtvLvkPZuc2JHOaZsjCvGSHFCuC3drUwN3YAc5_medium.webp"],"datasets":[{"label":"","data":[4,2,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[50,25,12.5,12.5],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Alferova V. A. et al. 4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides // Amino Acids. 2018. Vol. 50. No. 12. pp. 1697-1705.
GOST all authors (up to 50)
Copy
Alferova V. A., Shuvalov M. V., Suchkova T. A., Proskurin G. V., Aparin I. O., Rogozhin E. A., Novikov R. G., Solyev P. N., Chistov A. A., Ustinov A. V., Tyurin A. P., Korshun V. A. 4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides // Amino Acids. 2018. Vol. 50. No. 12. pp. 1697-1705.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1007/s00726-018-2642-3
UR - https://doi.org/10.1007%2Fs00726-018-2642-3
TI - 4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides
T2 - Amino Acids
AU - Alferova, Vera A
AU - Shuvalov, Maxim V
AU - Suchkova, Taisiya A
AU - Proskurin, Gleb V
AU - Aparin, Ilya O
AU - Novikov, Roman G.
AU - Solyev, Pavel N.
AU - Ustinov, Alexey V
AU - Tyurin, Anton P
AU - Korshun, Vladimir A.
AU - Rogozhin, Eugene A.
AU - Chistov, Alexey A
PY - 2018
DA - 2018/09/03 00:00:00
PB - Springer Nature
SP - 1697-1705
IS - 12
VL - 50
SN - 0939-4451
SN - 1438-2199
ER -
Cite this
BibTex
Copy
@article{2018_Alferova,
author = {Vera A Alferova and Maxim V Shuvalov and Taisiya A Suchkova and Gleb V Proskurin and Ilya O Aparin and Roman G. Novikov and Pavel N. Solyev and Alexey V Ustinov and Anton P Tyurin and Vladimir A. Korshun and Eugene A. Rogozhin and Alexey A Chistov},
title = {4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides},
journal = {Amino Acids},
year = {2018},
volume = {50},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007%2Fs00726-018-2642-3},
number = {12},
pages = {1697--1705},
doi = {10.1007/s00726-018-2642-3}
}
Cite this
MLA
Copy
Alferova, Vera A., et al. “4-Chloro-l-kynurenine as fluorescent amino acid in natural peptides.” Amino Acids, vol. 50, no. 12, Sep. 2018, pp. 1697-1705. https://doi.org/10.1007%2Fs00726-018-2642-3.