Diketo–ketoenol tautomers in curcuminoids: synthesis, separation of tautomers, and kinetic and structural studies

Osifová, Zuzana; Reiberger, Róbert; Císařová, I.; Machara, Aleš; Dračínský, Martin

doi:https://dx.doi.org/10.1021/acs.joc.2c01357

Number of the records: 1

Diketo–ketoenol tautomers in curcuminoids: synthesis, separation of tautomers, and kinetic and structural studies

1.

SYSNO ASEP	0559677
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Diketo–ketoenol tautomers in curcuminoids: synthesis, separation of tautomers, and kinetic and structural studies
Author(s)	Osifová, Zuzana (UOCHB-X) Reiberger, Róbert (UOCHB-X)_ORCID Císařová, I. (CZ) Machara, Aleš (UOCHB-X)_ORCID Dračínský, Martin (UOCHB-X)_{RID, ORCID}
Source Title	Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263 Roč. 87, č. 15 (2022), s. 10309-10318
Number of pages	10 s.
Language	eng - English
Country	US - United States
Keywords	NF-κB ; enol tautomerism ; NMR spectroscopy
OECD category	Organic chemistry
R&D Projects	GA22-15374S GA ČR - Czech Science Foundation (CSF)
	GA22-16389S GA ČR - Czech Science Foundation (CSF)
Method of publishing	Limited access
Institutional support	UOCHB-X - RVO:61388963
UT WOS	000837975900001
EID SCOPUS	85136141481
DOI	10.1021/acs.joc.2c01357
Annotation	Curcumin and its congeners exist in an equilibrium between diketo and ketoenol tautomers, which have different potencies to bind biomolecules. This work describes procedures for the preparation of 4-alkylated curcumin derivatives and the separation of their two tautomeric forms. Comprehensive NMR studies of the tautomer equilibria in various solvents have been accomplished. Additionally, a pure ketoenol tautomeric form of the active pharmaceutical ingredient (API) ASC-JM17 has been unequivocally determined by X-ray crystallography. Two different polymorphs of this API have been microscopically identified in the X-ray sample and manually separated, and a solid-state NMR study of the two polymorphs has also been performed. This work reports on the slow kinetics of diketo-ketoenol tautomerization in particular solvents that allow the separation and full characterization of both curcuminoids' tautomers.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418
Year of Publishing	2023
Electronic address	https://doi.org/10.1021/acs.joc.2c01357

Number of the records: 1