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  • Exploring the enantioseparation of amino-naphthol analogues by supercritical fluid chromatography.

Exploring the enantioseparation of amino-naphthol analogues by supercritical fluid chromatography.

Journal of chromatography. A (2015-02-18)
Anita Aranyi, István Ilisz, Antal Péter, Ferenc Fülöp, Caroline West
ABSTRACT

The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1-naphthol analogues and 2-(1-amino-2-methylpropyl)-1-naphthol) was investigated in supercritical fluid chromatography. Five commercially available chiral stationary phases based on immobilized polysaccharide chiral selectors (Chiralpak IA, IB, IC, ID and IE) were evaluated. Chiralpak IB was by far the most efficient to achieve the separation of these racemates and was further selected for optimization of elution conditions. The effects of column temperature (varying between 5 and 45 °C) and co-solvent added to carbon dioxide (methanol, ethanol, isopropanol and dichloromethane) were investigated. A particular attention was paid to mobile-phase additives. Several of them, acids, bases or salts (namely water, formic acid, acetic acid, trifluoroacetic acid, diethylamine, diethanolamine, triethylamine, triethanolamine, dimethylethanolamine, ammonia and ammonium acetate), were tested in order to improve peak shapes while maintaining selectivity. With the help of other achiral naphthol derivatives, the additive effects were examined.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Ammonia-14N, 99.99 atom % 14N
Sigma-Aldrich
1-Amino-2-methylpropan-2-ol, AldrichCPR
Sigma-Aldrich
Acetic acid-12C2, 99.9 atom % 12C
USP
Dehydrated Alcohol, United States Pharmacopeia (USP) Reference Standard
Supelco
Ethanol solution, certified reference material, 2000 μg/mL in methanol
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Acetic acid, analytical standard
Supelco
Ammonium acetate, LiChropur, eluent additive for LC-MS
Sigma-Aldrich
Diethanolamine, BioUltra, ≥99.5% (GC)
Sigma-Aldrich
Triethylamine, BioUltra, ≥99.5% (GC)
Sigma-Aldrich
Diethanolamine, puriss. p.a., ACS reagent, ≥99.0% (GC)
Supelco
Diethanolamine, analytical standard
Sigma-Aldrich
Triethylamine, for protein sequence analysis, ampule, ≥99.5% (GC)
Sigma-Aldrich
N,N-Diethylaniline, ≥99%
Sigma-Aldrich
Acetic acid, ≥99.5%, FCC, FG
Sigma-Aldrich
Diethanolamine, ACS reagent, ≥98.5%
Sigma-Aldrich
Ammonium acetate, reagent grade, ≥98%
Sigma-Aldrich
Ammonium acetate, BioXtra, ≥98%
Sigma-Aldrich
Ammonia, puriss., anhydrous, ≥99.95%
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Ammonium acetate solution, for molecular biology, 7.5 M
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Ammonia solution, 0.4 M in THF
Sigma-Aldrich
Ammonium acetate, for molecular biology, ≥98%
Sigma-Aldrich
Ammonium acetate, BioUltra, for molecular biology, ≥99.0%
Sigma-Aldrich
Ammonium acetate, 99.999% trace metals basis
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Triethylamine, for amino acid analysis, ≥99.5% (GC)
Sigma-Aldrich
Triethylamine, puriss. p.a., ≥99.5% (GC)
Sigma-Aldrich
Triethylamine, ≥99.5%
Sigma-Aldrich
Triethylamine, ≥99%
Sigma-Aldrich
Triethylamine, ≥99.5%
Supelco
Triethylamine, analytical standard
Sigma-Aldrich
Acetic acid, natural, ≥99.5%, FG