Home / Publications / Unusual stereoselectivity of methionine-γ-lyase from Citrobacterfreundii toward diastereomeric (S)-methionine S-oxide

Unusual stereoselectivity of methionine-γ-lyase from Citrobacterfreundii toward diastereomeric (S)-methionine S-oxide

Nikolai Grigoryevich Faleev 1
Nikolai Grigoryevich Faleev
, 
Marina Anatol'evna Tsvetikova 1
Marina Anatol'evna Tsvetikova
, 
Mikhail Mikhailovich Ilyin 1
Mikhail Mikhailovich Ilyin
, 
Vyacheslav Sergeyevich Yufryakov 1
Vyacheslav Sergeyevich Yufryakov
, 
Natal'ya Georgievna Kolotyrkina 2
Natal'ya Georgievna Kolotyrkina
, 
Viktoria V Kulikova 3
Viktoria V Kulikova
, 
Tatiana Victorovna Demidkina 3
Tatiana Victorovna Demidkina
, 
Konstantin Aleksandrovich Kochetkov 1, 4
Konstantin Aleksandrovich Kochetkov
10.1016/j.mencom.2021.03.030
Published 2021-03-03
Communication , Volume 31, Issue 2, 236-238
1
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Faleev N. G. et al. Unusual stereoselectivity of methionine-γ-lyase from Citrobacterfreundii toward diastereomeric (S)-methionine S-oxide // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 236-238.
GOST all authors (up to 50) Copy
Faleev N. G., Tsvetikova M. A., Ilyin M. M., Yufryakov V. S., Kolotyrkina N. G., Kulikova V. V., Demidkina T. V., Kochetkov K. A. Unusual stereoselectivity of methionine-γ-lyase from Citrobacterfreundii toward diastereomeric (S)-methionine S-oxide // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 236-238.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2021.03.030
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.030
TI - Unusual stereoselectivity of methionine-γ-lyase from Citrobacterfreundii toward diastereomeric (S)-methionine S-oxide
T2 - Mendeleev Communications
AU - Faleev, Nikolai Grigoryevich
AU - Tsvetikova, Marina Anatol'evna
AU - Ilyin, Mikhail Mikhailovich
AU - Yufryakov, Vyacheslav Sergeyevich
AU - Kolotyrkina, Natal'ya Georgievna
AU - Kulikova, Viktoria V
AU - Demidkina, Tatiana Victorovna
AU - Kochetkov, Konstantin Aleksandrovich
PY - 2021
DA - 2021/03/03
PB - Mendeleev Communications
SP - 236-238
IS - 2
VL - 31
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Faleev,
author = {Nikolai Grigoryevich Faleev and Marina Anatol'evna Tsvetikova and Mikhail Mikhailovich Ilyin and Vyacheslav Sergeyevich Yufryakov and Natal'ya Georgievna Kolotyrkina and Viktoria V Kulikova and Tatiana Victorovna Demidkina and Konstantin Aleksandrovich Kochetkov},
title = {Unusual stereoselectivity of methionine-γ-lyase from Citrobacterfreundii toward diastereomeric (S)-methionine S-oxide},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.030},
number = {2},
pages = {236--238},
doi = {10.1016/j.mencom.2021.03.030}
}
MLA
Cite this
MLA Copy
Faleev, Nikolai Grigoryevich, et al. “Unusual stereoselectivity of methionine-γ-lyase from Citrobacterfreundii toward diastereomeric (S)-methionine S-oxide.” Mendeleev Communications, vol. 31, no. 2, Mar. 2021, pp. 236-238. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.030.

Keywords

(S)-methionine S-oxide
diastereomers
kinetic resolution
methionine-γ-lyase
stereoselectivity

Abstract

Using a diastereomeric mixture of (S)-methionine S-oxide as an example, kinetic preference of methionine-γ-lyase toward a stereogenic center at the γ-sulfur atom of the (2S, RS) diastereomer was discovered for the first time.

References

1.
10.1016/j.mencom.2021.03.030_bib0005
Bornscheuer
Hydrolases in Organic Synthesis, 2006
2.
Advances in lipase-catalyzed esterification reactions
Stergiou P., Foukis A., Filippou M., Koukouritaki M., Parapouli M., Theodorou L.G., Hatziloukas E., Afendra A., Pandey A., Papamichael E.M.
Biotechnology Advances, 2013
8.
Michael additions of primary and secondary amines to acrylonitrile catalyzed by lipases
Souza R.O., Matos L.M., Gonçalves K.M., Costa I.C., Babics I., Leite S.G., Oestreicher E.G., Antunes O.A.
Tetrahedron Letters, 2009
9.
Immobilization of hog pancreas lipase in macroporous poly(vinyl alcohol)-cryogel carrier for the biocatalysis in water-poor media
Plieva F.M., Kochetkov K.A., Singh I., Parmar V.S., Belokon' Y.N., Lozinsky V.I.
Biotechnology Letters, 2000
10.
Immobilized Enzymes and Cells in Poly(N-Vinyl Caprolactam)-Based Hydrogels: Preparation, Properties, and Applications in Biotechnology and Medicine
Markvicheva E.A., Kuptsova S.V., Mareeva T.Y., Vikhrov A.A., Dugina T.N., Strukova S.M., Belokon Y.N., Kochetkov K.A., Baranova E.N., Zubov V.P., Poncelet D., Parmar V.S., Kumar R., Rumsh L.D.
Applied Biochemistry and Biotechnology, 2000
11.
Kochetkov K.A., Galkina M.A., Galkin O.M.
Mendeleev Communications, 2010
13.
Alferov K.V., Zhukov Y.N., Faleev N.G., Khurs E.N., Khomutov R.M.
Mendeleev Communications, 2003
14.
Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols
Kolodiazhna O.O., Kolodiazhna A.O., Kolodiazhnyi O.I.
Tetrahedron Asymmetry, 2013
17.
A versatile bacterial enzyme: l-methionine γ-lyase
Tanaka H., Esaki N., Soda K.
Enzyme and Microbial Technology, 1985
18.
Engineered Citrobacter freundii methionine γ-lyase effectively produces antimicrobial thiosulfinates
Morozova E.A., Kulikova V.V., Rodionov A.N., Revtovich S.V., Anufrieva N.V., Demidkina T.V.
Biochimie, 2016
19.
Mutant form C115H ofClostridium sporogenesmethionine γ-lyase efficiently cleaves S-Alk(en)yl-l-cysteine sulfoxides to antibacterial thiosulfinates
Kulikova V.V., Anufrieva N.V., Revtovich S.V., Chernov A.S., Telegin G.B., Morozova E.A., Demidkina T.V.
IUBMB Life, 2016
21.
The metabolic defect of methionine dependence occurs frequently in human tumor cell lines.
Mecham J.O., Rowitch D., Wallace C.D., Stern P.H., Hoffman R.M.
Biochemical and Biophysical Research Communications, 1983
23.
Efficacy of Recombinant Methioninase (rMETase) on Recalcitrant Cancer Patient-Derived Orthotopic Xenograft (PDOX) Mouse Models: A Review
Kawaguchi K., Han Q., Li S., Tan Y., Igarashi K., Murakami T., Unno M., Hoffman R.M.
Cells, 2019
26.
Identification of MsrA homologues for the preparation of (R)-sulfoxides at high substrate concentrations
Yang J., Wen Y., Peng L., Chen Y., Cheng X., Chen Y.
Organic and Biomolecular Chemistry, 2019
27.
New principle for palladacycle resolution: diastereoselective monomer to dimer conversion
Dunina V.V., Razmyslova E.D., Gorunova O.N., Livantsov M.V., Yuri K.Grishin
Tetrahedron Asymmetry, 2005
28.
First enantiopure imine CN-palladacycle of non-metallocenic planar chirality with the [2.2]paracyclophane backbone
Dunina V.V., Turubanova E.I., Livantsov M.V., Lyssenko K.A., Vorontsova N.V., Antonov D.Y., Grishin Y.K.
Tetrahedron Asymmetry, 2009