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

401757

Sigma-Aldrich

Tetrahydrofuran, anhydrous, ≥99.9%, inhibitor-free

612111

Supelco

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), NMR tube size 3 mm × 8 in.

704814

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 10 mM in D₂O ("100%", 99.96 atom % D), NMR tube size 5 mm × 7 in.

87369

Supelco

Tetrahydrofuran, Selectophore^™, ≥99.5%

78445

Supelco

Tetrahydrofuran, analytical standard

76887

Supelco

1,4-Dioxane, analytical standard

437638

Sigma-Aldrich

Tetrahydrofuran, contains 250 ppm BHT as inhibitor, ACS reagent, ≥99.0%

186562

Sigma-Aldrich

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

439215

Sigma-Aldrich

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

296309

Sigma-Aldrich

1,4-Dioxane, anhydrous, 99.8%, contains <=25 ppm BHT as stabilizer

551368

Sigma-Aldrich

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

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.

676764

Sigma-Aldrich

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

360481

Sigma-Aldrich

1,4-Dioxane, ACS reagent, ≥99.0%, contains ≤25 ppm BHT as stabilizer

360589

Sigma-Aldrich

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

676934

Sigma-Aldrich

1,4-Dioxane, ACS reagent, ≥99.0%, contains <=25 ppm BHT as stabilizer

33147

Sigma-Aldrich

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

178810

Sigma-Aldrich

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

87368

Sigma-Aldrich

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

D201863

Sigma-Aldrich

1,4-Dioxane, ReagentPlus^®, ≥99%, contains ≤25 ppm BHT as stabilizer

34865

Sigma-Aldrich

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

34857

Sigma-Aldrich

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

CRM48367

Supelco

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

02575

Supelco

Dichloromethane, analytical standard

66742

Supelco

Dichloromethane, Selectophore^™, ≥99.5%

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

M1550000

Methylene chloride, European Pharmacopoeia (EP) Reference Standard

676853

Sigma-Aldrich

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

D65100

Sigma-Aldrich

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