Analysis by RP-HPLC and Purification by RP-SPE of the C-Tetra(p-hydroxyphenyl)resorcinolarene Crown and Chair Stereoisomers

Castillo-Aguirre, Alver; Rivera‐Monroy, Zuly Jenny; Maldonado, Mauricio

doi:10.1155/2019/2051282

Cited by 7 publications

(8 citation statements)

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“…The products were purified by means of recrystallization, and the derivatives were characterized using spectral techniques, including FT-IR, 1 H NMR, 13 C NMR, and mass spectrometry. These compounds have been previously synthesized, and the spectroscopic data agreed with those reported by us [30,31,33,34].…”

Section: Resultssupporting

confidence: 84%

“…Continuing with our research on the synthesis and functionalization of calix[4]resorcinarenes [31,32,33,34,35] and on the modification of polymeric surfaces [30], in this article we study the synthesis and use of aminomethylated-calix[4]resorcinarenes in the functionalization of glycidyl methacrylate copolymers and their application in the interaction with peptides.…”

Section: Introductionmentioning

confidence: 99%

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Aminomethylated Calix[4]resorcinarenes as Modifying Agents for Glycidyl Methacrylate (GMA) Rigid Copolymers Surface

et al. 2019

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Functionalization of tetrapropylcalix[4]resorcinarene, tetrapentylcalix[4]resorcinarene, tetranonylcalix[4]resorcinarene, and tetra-(4-hydroxyphenyl)calix[4]resorcinarene by means of aminomethylation reactions with the amino acids β-alanine and l-proline in the presence of aqueous formaldehyde was carried out. When β-alanine was used, the reaction products were tetrabenzoxazines. The reaction with tetra-(4-hydroxyphenyl)calix[4]resorcinarene did not proceed under the experimental conditions; therefore, l-proline was used, and the corresponding tetra-Mannich base was regio- and diasteroselectively formed. The products were characterized via FT-IR, 1H NMR, 13C NMR, and elemental analysis. With these aminomethylated-calix[4]resorcinarenes, the chemical surface modification of the copolymers poly(GMA–co–EDMA) and poly(BMA–co–EDMA–co–MMA) in a basic medium was studied. The results were quite satisfactory, obtaining the corresponding copolymers functionalized by nucleophilic substitution reaction and ring-opening between the carboxyl group of the upper rim of aliphatic calix[4]resorcinarenes and the hydroxyl group of the lower rim in the aromatic calix[4]resorcinarene and the epoxy group of the glycidyl methacrylate residue of each copolymer. The modified copolymers were characterized via FT-IR, scanning electron microscopy imaging, and elemental analysis. Finally, the modified copolymer surfaces exhibited interaction with peptides, showing their potential application in chromatographic separation techniques such as high-performance liquid chromatography.

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Section: Resultssupporting

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Aminomethylated Calix[4]resorcinarenes as Modifying Agents for Glycidyl Methacrylate (GMA) Rigid Copolymers Surface

et al. 2019

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“…For the present study, we chose the resorcinarenes tetranonylresorcinarene ( 3 ) and tetra(4-hydroxyphenyl)resorcinarene ( 4 ) for the aminomethylation reaction with chiral aminocompounds ( S )-(-)-1-phenylethylamine and l -proline. The synthesis of resorcinarenes 3 and 4 was carried out starting from resorcinol with the respective aldehyde in a mixture of ethyl alcohol and water (1:1) at reflux, in accordance with how it is described in the literature and as we have previously developed it [34,35]. Once the resorcinarene tetranonylresorcinarene ( 3 ) was obtained, the first step involved reaction with the chiral amine ( S )-(-)-1-phenylethylamine in presence of formaldehyde via base-catalyzed cyclocondensation, as per the method described in the literature (Scheme 2) [43].…”

Section: Resultsmentioning

confidence: 99%

“…The preparation of starting resorcinarenes tetranonylresorcinarene (3) and tetra-(4-hydroxyphenyl)resorcinarene ( 4 ) was performed in accordance with previous studies [34,35]. The functionalization of 3 and 4 was developed based on previous research [33].…”

Section: Methodsmentioning

confidence: 99%

“…Continuing with our research on the synthesis and functionalization of resorcinarenes [34,35,36] and on the modification of polymeric materials [32,33], in this article we study the chemical and physical modification of methacrylate-based polymers with chiral resorcinarenes and their application as extractive phases for norepinephrine microextraction.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Methacrylate-Based Polymers Modified with Chiral Resorcinarenes and Their Evaluation as Sorbents in Norepinephrine Microextraction

Castillo-Aguirre

Maldonado

2019

Polymers

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Aminomethylation reactions between chiral amino compounds (S)-(-)-1-phenylethylamine and l-proline with tetranonylresorcinarene and tetra-(4-hydroxyphenyl)resorcinarene in presence of formaldehyde were studied. The reaction between l-proline and resorcinarenes generated regioselectively chiral tetra-Mannich bases, due to the molecular incorporation of the fragment of the chiral amino acid. On the other hand, tetranonylresorcinarene and (S)-(-)-1-phenylethylamine formed regio- and diasteroselectively chiral tetrabenzoxazines, both by chiral auxiliary functionalization and by the transformation of the molecular structure that confers inherent chirality. The products obtained were characterized using IR, 1H-NMR, 13C-NMR, COSY, HMQC, and HMBC techniques. The reaction of (S)-(-)-1-phenylethylamine with tetra-(4-hydroxyphenyl)resorcinarene did not proceed under the experimental conditions. Once the chiral aminomethylated tetra-(4-hydroxyphenyl)resorcinarene was obtained, the chemical modification of poly(GMA–co–EDMA) was studied, and the results showed an efficient incorporation of the aminomethylated compound. For the physical modification, chiral aminomethylated tetranonylresorcinarenes were employed, finding that the incorporation of modified resorcinarenes occurs, but with less efficiency than that observed using chemical modification. The modified polymers were characterized via FT-IR, scanning electron microscopy imaging, and elemental analysis. Finally, polymers modified with chiral resorcinarenes were used as sorbents in norepinephrine microextraction; for practical purposes, artificial urine was prepared and used. To perform the microextraction, the decision was made to use the modern rotating-disk sorptive extraction technique (RDSE), because of its analytical attributes as a green, or eco-friendly, technique. According to the results, the method preliminarily validated for the determination of norepinephrine in artificial urine shows that the modified polymer with chiral derivative of tetra-(4-hydroxyphenyl)resorcinarene worked effectively as a new sorbent phase for the quantitative microextraction of norepinephrine, exhibiting high stability and homogeneity of composition and structure within the working range.

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DMSO-controlled self-assembly of supramolecular structures of aryl-resorcinarenes

Castillo-Aguirre

Sanabria

Maldonado

et al. 2023

Journal of Molecular Liquids

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Analysis by RP-HPLC and Purification by RP-SPE of the C-Tetra(p-hydroxyphenyl)resorcinolarene Crown and Chair Stereoisomers

Cited by 7 publications

References 35 publications

Aminomethylated Calix[4]resorcinarenes as Modifying Agents for Glycidyl Methacrylate (GMA) Rigid Copolymers Surface

Aminomethylated Calix[4]resorcinarenes as Modifying Agents for Glycidyl Methacrylate (GMA) Rigid Copolymers Surface

Preparation of Methacrylate-Based Polymers Modified with Chiral Resorcinarenes and Their Evaluation as Sorbents in Norepinephrine Microextraction

DMSO-controlled self-assembly of supramolecular structures of aryl-resorcinarenes

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