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Enantioselective synthesis of 5-fluoro-L-DOPA via chemoenzymatic route

Konstantin Aleksandrovich Kochetkov 1, 2
Konstantin Aleksandrovich Kochetkov
, 
Marina Anatol'evna Tsvetikova 2
Marina Anatol'evna Tsvetikova
, 
Olga Nikolaevna Gorunova 2
Olga Nikolaevna Gorunova
, 
Nataliya Anatol'evna Bystrova 2
Nataliya Anatol'evna Bystrova
, 
Vyacheslav Sergeyevich Yufriakov 2
Vyacheslav Sergeyevich Yufriakov
1 D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation
2 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
10.1016/j.mencom.2024.01.003
Published 2023-12-25
Communication , Volume 34, Issue 1, 11-12
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Kochetkov K. A. et al. Enantioselective synthesis of 5-fluoro-L-DOPA via chemoenzymatic route // Mendeleev Communications. 2023. Vol. 34. No. 1. pp. 11-12.
GOST all authors (up to 50) Copy
Kochetkov K. A., Tsvetikova M. A., Gorunova O. N., Bystrova N. A., Yufriakov V. S. Enantioselective synthesis of 5-fluoro-L-DOPA via chemoenzymatic route // Mendeleev Communications. 2023. Vol. 34. No. 1. pp. 11-12.
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TY - JOUR
DO - 10.1016/j.mencom.2024.01.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.003
TI - Enantioselective synthesis of 5-fluoro-L-DOPA via chemoenzymatic route
T2 - Mendeleev Communications
AU - Kochetkov, Konstantin Aleksandrovich
AU - Tsvetikova, Marina Anatol'evna
AU - Gorunova, Olga Nikolaevna
AU - Bystrova, Nataliya Anatol'evna
AU - Yufriakov, Vyacheslav Sergeyevich
PY - 2023
DA - 2023/12/25
PB - Mendeleev Communications
SP - 11-12
IS - 1
VL - 34
ER -
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@article{2023_Kochetkov,
author = {Konstantin Aleksandrovich Kochetkov and Marina Anatol'evna Tsvetikova and Olga Nikolaevna Gorunova and Nataliya Anatol'evna Bystrova and Vyacheslav Sergeyevich Yufriakov},
title = {Enantioselective synthesis of 5-fluoro-L-DOPA via chemoenzymatic route},
journal = {Mendeleev Communications},
year = {2023},
volume = {34},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.003},
number = {1},
pages = {11--12},
doi = {10.1016/j.mencom.2024.01.003}
}
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Kochetkov, Konstantin Aleksandrovich, et al. “Enantioselective synthesis of 5-fluoro-L-DOPA via chemoenzymatic route.” Mendeleev Communications, vol. 34, no. 1, Dec. 2023, pp. 11-12. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.003.
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Keywords

5-fluoro-L-DOPA
5-fluoro-L-tyrosine
Amino acids.
Chemoenzymatic method
enantioselective synthesis
organofluorine compounds
Tyrosin phenol lyase

Abstract

The title compound, 5-fluoro-3,4-dihydroxy-L-phenylalanine, was prepared in four steps, with the key step having been the enantiospecific production of 5-fluoro-L-tyrosine by the chemoenzymatic reaction between 2-fluorophenol, potassium pyruvate and ammonia promoted by the live culture of Citrobacter freundii cells. 5-Fluoro-L-tyrosine was hydroxylated by sequential nitration, reduction and diazotization followed by hydrolysis.

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