Chiral separations by HPLC on immobilized polysaccharide chiral stationary phases.

Chiral separations by HPLC on immobilized polysaccharide chiral stationary phases.

Methods in molecular biology (Clifton, N.J.) (2013-01-04)

Imran Ali, Zeid A Al-Othman, Hassan Y Aboul-Enein

ABSTRACT

Immobilized polysaccharide chiral stationary phases (CSPs) are a new development in chiral chromatography with increasing importance for the resolution of racemic compounds. These CSPs can be used with solvents traditionally applied for the classical coated polysaccharide CSPs as well as solvents that were "forbidden" for the coated phases such as tetrahydrofuran, chloroform, dichloromethane, acetone, 1,4-dioxane, ethylacetate, and certain ethers. However, these forbidden solvents may be required for the determination of the chiral recognition mechanism. Therefore, the immobilized CSPs are effective for the evaluation of chiral recognition mechanisms. Furthermore, immobilized chiral columns are also useful for monitoring the progress of stereospecific synthetic reactions which are normally performed in such solvents. The present chapter describes the detailed experimental protocol of a chiral resolution on immobilized polysaccharides CSPs by HPLC.

MATERIALS

Product Number

Brand

Product Description

178810

Sigma-Aldrich

Tetrahydrofuran, ≥99.0%, contains 200-400 ppm BHT as inhibitor, ReagentPlus^®

684228

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), NMR tube size 10 mm × 8 in.

551368

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D)

270385

Supelco

Tetrahydrofuran, HPLC grade, ≥99.9%, inhibitor-free

611905

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 5 mm × 8 in.

631833

Supelco

1,4-Dioxane solution, suitable for NMR (reference standard), 5 mM in benzene-d₆ (99.6 atom % D), NMR tube size 3 mm × 8 in.

736171

Supelco

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), NMR tube size 5 mm × 8 in.

33147

Sigma-Aldrich

1,4-Dioxane, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.5% (GC)

76887

Supelco

1,4-Dioxane, analytical standard

CRM48367

Supelco

1,4-Dioxane solution, certified reference material, 2000 μg/mL in methanol, ampule of 1 mL

401757

Sigma-Aldrich

Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free

D201863

Sigma-Aldrich

1,4-Dioxane, ReagentPlus^®, ≥99%, contains ≤50 ppm BHT as stabilizer

87368

Sigma-Aldrich

Tetrahydrofuran, contains 250 ppm BHT as inhibitor, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.9%

186562

Sigma-Aldrich

Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%

34857

Sigma-Aldrich

1,4-Dioxane, suitable for HPLC, ≥99.5%

34865

Sigma-Aldrich

Tetrahydrofuran, inhibitor-free, suitable for HPLC, ≥99.9%

78445

Supelco

Tetrahydrofuran, analytical standard

87369

Supelco

Tetrahydrofuran, Selectophore^™, ≥99.5%

360589

Sigma-Aldrich

Tetrahydrofuran, contains 200-400 ppm BHT as inhibitor, ACS reagent, ≥99.0%

360481

Sigma-Aldrich

1,4-Dioxane, ACS reagent, ≥99.0%, contains ≤50 ppm BHT as stabilizer

631868

Supelco

1,4-Dioxane solution, suitable for NMR (reference standard), 5 mM in chloroform-d (99.8 atom % D), NMR tube size 3 mm × 8 in.

676853

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

270997

Sigma-Aldrich

Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer

439223

Sigma-Aldrich

Dichloromethane, suitable for HPLC, ≥99.9%, contains 40-150 ppm amylene as stabilizer

32222

Sigma-Aldrich

Dichloromethane, puriss. p.a., ACS reagent, reag. ISO, ≥99.9% (GC)

24233

Sigma-Aldrich

Dichloromethane, puriss., meets analytical specification of Ph. Eur., NF, ≥99% (GC)

02575

Supelco

Dichloromethane, analytical standard

320269

Sigma-Aldrich

Dichloromethane, ACS reagent, ≥99.5%, contains 40-150 ppm amylene as stabilizer

650463

Sigma-Aldrich

Dichloromethane, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains 50-150 ppm amylene as stabilizer

66742

Supelco

Dichloromethane, Selectophore^™, ≥99.5%