» Articles » PMID: 36643487

Efficient Separation of C-Tetramethylcalix[4]resorcinarene Conformers by Means of Reversed-Phase Solid-Phase Extraction

Overview
Journal ACS Omega
Specialty Chemistry
Date 2023 Jan 16
PMID 36643487
Authors
Affiliations
Soon will be listed here.
Abstract

A reversed-phase high-performance liquid chromatography (RP-HPLC) method was developed to study the conformer formation generated during the reaction for obtaining -tetramethylcalix[4]resorcinarene. The chromatographic method was used to design a strategy for purifying the reaction products, using solid-phase extraction columns (RP-SPE) and gradient elution. The chromatographic profiles of the cyclocondensation reaction between resorcinol and acetaldehyde show the presence of three products under the different reaction and precipitation conditions studied. Using RP-SPE, it was possible to enrich the products, which were later characterized by means of RP-HPLC and H nuclear magnetic resonance (NMR). This investigation explored and established a new method for RP-HPLC analysis and RP-SPE separation of conformational isomers obtained in the formation reaction of -tetramethylcalix[4]resorcinarene.

Citing Articles

Thermally-induced atropisomerism promotes metal-organic cage construction.

Liang J, Lu S, Yang Y, Shen Y, Bai J, Sun X Nat Commun. 2023; 14(1):8166.

PMID: 38071355 PMC: 10710450. DOI: 10.1038/s41467-023-43756-4.


Peptide-Resorcinarene Conjugates Obtained via Click Chemistry: Synthesis and Antimicrobial Activity.

Pineda-Castaneda H, Maldonado-Villamil M, Marcela Parra-Giraldo C, Lucia Leal-Castro A, Fierro-Medina R, Rivera-Monroy Z Antibiotics (Basel). 2023; 12(4).

PMID: 37107135 PMC: 10135297. DOI: 10.3390/antibiotics12040773.

References
1.
Insuasty Cepeda D, Pineda Castaneda H, Rodriguez Mayor A, Castaneda J, Maldonado Villamil M, Medina R . Synthetic Peptide Purification via Solid-Phase Extraction with Gradient Elution: A Simple, Economical, Fast, and Efficient Methodology. Molecules. 2019; 24(7). PMC: 6479624. DOI: 10.3390/molecules24071215. View

2.
He M, Johnson R, Escobedo J, Beck P, Kim K, St Luce N . Chromophore formation in resorcinarene solutions and the visual detection of mono- and oligosaccharides. J Am Chem Soc. 2002; 124(18):5000-9. PMC: 3386614. DOI: 10.1021/ja017713h. View

3.
Ma B, Coppens P . Transformation of a C-methylcalix[4]resorcinarene-based host-guest complex from a wave-like to a novel triangular brick-wall architecture. Chem Commun (Camb). 2003; (4):504-5. DOI: 10.1039/b212548j. View

4.
Espanol E, Maldonado Villamil M . Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules. Biomolecules. 2019; 9(3). PMC: 6468619. DOI: 10.3390/biom9030090. View

5.
Castillo-Aguirre A, Rivera Monroy Z, Maldonado M . Analysis by RP-HPLC and Purification by RP-SPE of the -Tetra(-hydroxyphenyl)resorcinolarene and Stereoisomers. J Anal Methods Chem. 2019; 2019:2051282. PMC: 6501146. DOI: 10.1155/2019/2051282. View