Bidentate Lactate Binding to La(III)-Cu(II) Metallacrown with L-Phenylalaninehydroximate Ligands: the Chiral Separation of L-Lactate

Marina A. Katkova,^@ Evgeny V. Baranov, Galina S. Zabrodina, and Sergey Yu. Ketkov

G.A. Razuvaev Institute of Organometallic Chemistry of RAS, 603905 Nizhny Novgorod, Russia

^@Corresponding author E-mail: marina@iomc.ras.ru

DOI: 10.6060/mhc200816k

Macroheterocycles 2021 14(1) 101-104

The chiral La(III)-Cu(II) metallacrown bearing L-phenylalaninehydroximate ligands was probed for complexation towards racemic lactate. X-Ray diffraction analysis revealed the bidentate chelation of L-lactate in the solid state to form enantiopure crystals. L-Phenylalaninehydroximate La(III)-Cu(II) metallacrown showed, therefore, a strong preference for coordination of the L-type lactate providing the chiral separation of the target compound.

References:

Click here to expand or collapse this section

1. a) Gropp C., Quigley B.L., Diederich F. J. Am. Chem. Soc. 2018, 140, 2705-2717;
https://doi.org/10.1021/jacs.7b12894
(b) Zhong D.C., Lu T.B. Chem. Commun. 2016, 52, 10322-10337.
https://doi.org/10.1039/C6CC03660K

2. (a) Bodwin J.J., Cutland A.D., Malkani R.G., Pecoraro V.L. Coord. Chem. Rev. 2001, 216-217, 489-512;
https://doi.org/10.1016/S0010-8545(00)00396-9
(b) Mezei G., Zaleski C.M., Pecoraro V.L. Chem. Rev. 2007, 107, 4933-5003;
https://doi.org/10.1021/cr078200h
(c) Tegoni M., Remelli M. Coord. Chem. Rev. 2012, 256, 289-315;
https://doi.org/10.1016/j.ccr.2011.06.007
(d) Happa P., Plenka C., Rentschler E. Coord. Chem. Rev., 2015, 289-290, 238-260;
https://doi.org/10.1016/j.ccr.2014.11.012
(e) Ostrowska M., Fritsky I.O., Gumienna-Kontecka E., Pavlishchuk A.V. Coord. Chem. Rev., 2016, 327-328, 304-332;
https://doi.org/10.1016/j.ccr.2016.04.017
(f) Katkova M.A. Russ. J. Coord. Chem. 2018, 44, 284-300.
https://doi.org/10.1134/S107032841804005X

3. (a) Stemmler A.J., Barwinski A., Baldwin M.J., Young V., Pecoraro V.L. J. Am. Chem. Soc. 1996, 118, 11962-11963;
https://doi.org/10.1021/ja9622968
(b) Katkova M.A., Zabrodina G.S., Zhigulin G.Yu., Rumyantsev R.V., Ketkov S.Yu. Russ. J. Coord. Chem. 2019, 45, 721-727.
https://doi.org/10.1134/S1070328419100014

4. (a) Makarov S.G., Zabrodina G.S., Cherkasov A.V., Plyusnin P.E., Arapova A.V., Katkova M.A., Ketkov S.Yu. Macroheterocycles 2016, 9, 263-267;
https://doi.org/10.6060/mhc160317m
(b) Zabrodina G.S., Katkova M.A., Samsonov M.A., Ketkov S.Yu. Z. Anorg. Allg. Chem. 2018, 644, 907-911;
https://doi.org/10.1002/zaac.201800214
(c) Katkova M.A., Zabrodina G.S., Baranov E.V., Muravyeva M.S., Kluev E.A., Shavyrin A.S., Zhigulin G.Yu., Ketkov S.Yu. Appl. Organomet. Chem. 2018, 32, e4389;
https://doi.org/10.1002/aoc.4389
(d) Katkova M.A., Zabrodina G.S., Rumyantcev R.V., Zhigulin G.Yu., Ketkov S.Yu., Lyssenko K.A., Fomina I.G., Eremenko I.L. Eur. J. Inorg. Chem. 2019, 2019, 4328-4335.
https://doi.org/10.1002/ejic.201900536

5. Staszak K., Wieszczycka K., Marturano V., Tylkowski B. Coord. Chem. Rev., 2019, 397, 76-90.
https://doi.org/10.1016/j.ccr.2019.06.017

6. Sheldrick G.M. SADABS v.2016/2, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. 2016.

7. Sheldrick G.M. Acta Cryst., 2015, A71, 3-8.
https://doi.org/10.1107/S2053229614024218

8. Bruker. SAINT Data Reduction and Correction Program v. 8.38A, Bruker AXS, Madison, Wisconsin, USA. 2017.

9. Sheldrick G.M., SHELXTL. Version 6.14. Structure Determination Software Suite; Madison (WI, USA): Bruker AXS, 2003.

10. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H., J. Appl. Cryst., 2009, 42, 339-341.
https://doi.org/10.1107/S0021889808042726

Attachment	Size
mhc200816k.pdf	1.16 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Bidentate Lactate Binding to La(III)-Cu(II) Metallacrown with L-Phenylalaninehydroximate Ligands: the Chiral Separation of L-Lactate

References: