Skip to Content
MilliporeSigma
  • 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

Supelco
Methanol, analytical standard
Supelco
Ethanol solution, certified reference material, 2000 μg/mL in methanol
Sigma-Aldrich
Diethanolamine, BioUltra, ≥99.5% (GC)
Sigma-Aldrich
Diethanolamine, puriss. p.a., ACS reagent, ≥99.0% (GC)
Sigma-Aldrich
Ammonia, anhydrous, ≥99.98%
Sigma-Aldrich
Methanol, anhydrous, 99.8%
Supelco
Ammonium acetate, LiChropur, eluent additive for LC-MS
Sigma-Aldrich
Triethylamine, BioUltra, ≥99.5% (GC)
Supelco
Diethanolamine, analytical standard
Sigma-Aldrich
Triethylamine, for protein sequence analysis, ampule, ≥99.5% (GC)
Sigma-Aldrich
Diethanolamine, ACS reagent, ≥98.5%
Sigma-Aldrich
N,N-Diethylaniline, ≥99%
Sigma-Aldrich
Acetic acid, for luminescence, BioUltra, ≥99.5% (GC)
Sigma-Aldrich
Methanol, suitable for HPLC, gradient grade, 99.93%
Sigma-Aldrich
Acetic acid, ≥99.5%, FCC, FG
Sigma-Aldrich
Ethanol Fixative 80% v/v, suitable for fixing solution (blood films)
Sigma-Aldrich
Ammonium acetate, reagent grade, ≥98%
Sigma-Aldrich
Ammonium acetate, BioXtra, ≥98%
Sigma-Aldrich
Ammonium acetate solution, for molecular biology, 7.5 M
Sigma-Aldrich
Ammonia-14N, 99.99 atom % 14N
Sigma-Aldrich
Methanol, HPLC Plus, ≥99.9%, poly-coated bottles
Sigma-Aldrich
Acetic acid-12C2, 99.9 atom % 12C
Sigma-Aldrich
Ammonia solution, 0.4 M in THF
Sigma-Aldrich
Methanol, JIS 300, ≥99.8%, for residue analysis
Sigma-Aldrich
Ammonium acetate solution, 50 % (w/v), for copper determination
Sigma-Aldrich
Ammonium acetate solution, BioUltra, for molecular biology, ~5 M in H2O
Supelco
Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Acetic acid, ≥99.7%
Sigma-Aldrich
Diethanolamine, SAJ first grade, ≥98.0%
Sigma-Aldrich
Triethylamine, SAJ first grade, ≥98.0%