COSMOSIL CHiRAL Series

Transcription

1 Immobilized Polysaccharide Derivative-Based Chiral Columns CSMSIL CiRAL Series Immobilized chiral selectors can withstand many different solvents Sharpen peaks with 3 μm particles Preparative separations with 5 μm particles Equivalent performance to columns currently on the market Competitive price Conceptual Model CSMSIL CiRAL Series Packing Material CSMSIL CiRAL 3A, 5A USP Code Base Material Particle Size Chiral Selector CSMSIL CiRAL 3B, 5B CSMSIL CiRAL 3C, 5C Silica gel 3, 5 μm Cellulose tris (3,5-dimethylphenyl carbamate) Cellulose tris (3,5-dichlorophenyl carbamate) L99 Amylose tris (3,5-dimethylphenyl carbamate) R R R R R R R R R n n Chiral Selector Type Usable p Range CI R= n R= Immobilized 2-9 R= CI

2 Immobilized Stationary Phase igh Resistance to Solvents The CSMSIL CiRAL series uses a chiral selector that is chemically bonded to the silica gel, which results in high resistance to solvents. Tetrahydrofuran (TF) strips coated selectors from the stationary phase, reducing theoretical plates to less than 1/5 in our experiment. owever, the same selectors bonded to the silica withstood repeated injections of TF. Comparison: Coated and Immobilized Selectors Detection: UV270nm Company A, Type B (Coated) (o.2) : 16,000 (o.2) : 2,900 trans-stilbene oxide (0.5mg/ml) 10µl TF 100µ 5 injections CSMSIL CiRAL 3B (o.2) : 20,900 (o.2) : 19,600 TF 100µ 5 injections Usable Solvents Due to its immobilized selectors, various solvents are usable with CSMSIL CiRAL. A wide variety of solvents increases your selectivity options. Solvent Immobilized Coated Selectivity Depends on the Solvent ormal phase Reversed phase ormal phase CSMSIL CiRAL 3B, 4.6 mm I.D. x 250 mm n-exane * * 1-Acenaphthenol n-eptane Methanol exane / Ethanol * * = 97 / 3 = 1.09 Ethanol 2-Propanol (Isopropanol) Acetonitrile * * Tetrahydrofuran (TF) t-butyl methyl ether Toluene Chloroform Dichloromethane (Methylene chloride) Ethyl acetate Water Aqueous buffer exane / 2-Propanol = 95 / 5 exane / Tetrahydrofuran = 90 / 10 exane / Chloroform = 65 / 35 exane / t-butylmethylether = 60 / 40 〇 Usable Unusable * Methanol / acetonitrile and n-hexane are not miscible with each other, so they should not be mixed for LC. Elution strength: alcohols, TF >> chloroform > t-butyl methyl ether >> alkanes = 1.08 = 1.14 = 1.24 = 1.32

3 Available in 3 μm Particles Sharp Peaks CSMSIL CiRAL columns are available in 3 μm particles, which yield sharper peaks than conventional 5 μm particles. Columns for preparative separations are available with 5 μm particles. Comparison : 5 μm/3 μm (1) Flavanone (0.5mg/ml) Company U Type B (5μm) (Last peak) : CSMSIL CiRAL3B (3μm) (Last peak) : 21,000 Comparison : 5 μm/3 μm (2) Ketoprofen (0.3mg/ml) Company U, Type C (5μm) (Last peak) : CSMSIL CiRAL 3C (3μm) (Last peak) : Moderate Backpressure The CSMSIL CiRAL 3 series (3 μm particles) puts moderately higher pressure on the system compared to conventional 5 μm particles. This improves reproducibility for low-pressure solvents, such as hexane, that may otherwise cause pump irregularities. As shown in the figure below, increased 2-propanol concentration causes higher pressure. owever, even at 50% (v/v), the pressure did not exceed 12 MPa. At the lowest concentration of 5% (v/v), the backpressure was 5.3 MPa. This range allows high flexibility in mobile phase composition and selectivity. Pressure (MPa) Pressure vs. mobile phase composition CSMSIL CiRAL 3A, CSMSIL CiRAL 5A, Conditions Packing material: CSMSIL CiRAL 3A (3μm) CSMSIL CiRAL 5A (5μm) Column size: 4.6 mm I.D. x 250 mm Mobile phase: exane / 2-Propanol (ratio as in figure) Temperature: Propanol conc. (%)

4 Equivalent Separation to Competitors Columns The CSMSIL CiRAL 5 series (5 μm particles) is equivalent to other companies immobilized polysaccharide derivativebased chiral columns. Chiral selector: Amylose tris (3,5-dimethylphenyl carbamate) [Type A] CSMSIL Application Data Ketoprofen (0.3mg/ml) CSMSIL CiRAL 5A Chiral selector: Cellulose tris (3,5-dimethylphenyl carbamate) [Type B] CSMSIL Application Data Flavanone (0.5mg/ml) Company U, Type B CSMSIL CiRAL 5B Chiral selector: Cellulose tris (3,5-dichlorophenyl carbamate) [Type C] CSMSIL Application Data DL-MandelicAcid (10mg/ml) 2.0µl Company U, Type C CSMSIL CiRAL5C

5 Same Selectivity with Identical Chiral Selectors The same chiral selector will yield similar separation patterns. In general, Enantiomers that can be separated on a coated selector can also be separated on an immobilized selector, and those that cannot be separated on one will not be separated on the other. Chiral selector: Amylose tris (3,5-dimethylphenyl carbamate) [Type A] CSMSIL Application Data CSMSIL CiRAL 5A Mobile phase: n-exane / 2-Propanol = 95/5 Coated 1-(2-aphthyl)ethanol (2.0mg/ml) 1.0µl Chiral selector: Amylose tris (3,5-dimethylphenyl carbamate) [Type A] CSMSIL Application Data CSMSIL CiRAL 5A Mobile phase: n-exane / 2-Propanol / Diethylamine = 95/5/0.1 Detection: UV225nm Coated 1,2-Diphenylethylamine (1.0mg/ml) 1.5µl 2 Chiral selector: Cellulose tris (3,5-dimethylphenyl carbamate) [Type B] CSMSIL Application Data Company U, Type B Company U, Type B CSMSIL CiRAL 5B Coated Ketoprofen (0.3mg/ml)

6 Column Selection CSMSIL CiRAL offers 3 different chiral selectors that, together, have a high probability of separating your sample. f 28 samples in our test, 27 pairs of enantiomers were fully separated. For samples that do not separate easily with any column, please adjust the type and concentration of solvents in your mobile phase. Sample, mobile phase CSMSIL CiRAL A CSMSIL CiRAL B CSMSIL CiRAL C trans-stillbene oxide Complete Separation Complete Separation Complete Separation exane / 2-Propanol = 90 / 10 2-(2,4-Dichlorophenoxy) propionic acid Complete Separation Complete Separation Cl Cl 3 C * exane / 2-Propanol / TFA = 95 / 5 / (1-aphthyl)ethanol 3 C * Complete Separation Complete Separation exane / 2-Propanol = 90 / 10 icardipine 3 C Complete Separation 3 C * 2 exane / 2-Propanol / Diethylamine = 90 / 10 / 0.1 Chiral selector hit rate*(n = 28) 60.7% 67.9% 71.4% * Complete separation (hit) is defined as the two enantiomer peaks having resolution (R S ) greater than or equal to 1.5. The best separation for each sample is marked with double rings.

7 Application Data eutral Compounds Methyl DL-Mandelate 1,1 -Bi-2-naphthol CSMSIL Application Data CSMSIL Application Data CSMSIL CiRAL 3B Detection: UV220nm Methyl DL-Mandelate (1.0mg/ml) 0.75µl CSMSIL CiRAL 3C Detection: UV335nm 1,1 -Bi-2-naphthol (0.5mg/ml) 1.5µl Acidic Compounds To prevent tailing and lack of detection, add an appropriate acid to the mobile phase (about 0.1%). -Carbobenzoxy-DL-alanine Mecoprop CSMSIL Application Data CSMSIL Application Data CSMSIL CiRAL 3B Detection: UV210nm CSMSIL CiRAL 3A Mobile phase: n-exane / 2-Propanol / TFA = 95/5/0.1 Detection: UV230nm -Carbobenzoxy-DL-alanine (0.5mg/ml) 0.75µl Mecoprop (0.5mg/ml) 0.5µl 3C Cl Basic Compounds To prevent tailing and lack of detection, add an appropriate base to the mobile phase (about 0.1%). Carbinoxamine Tramadol CSMSIL Application Data CSMSIL Application Data CSMSIL CiRAL 3A Mobile phase: n-exane / 2-Propanol / Diethylamine = 90/10/0.1 Detection: UV225nm CSMSIL CiRAL 3C Mobile phase: n-exane / 2-Propanol / Diethylamine = 95/5/0.1 Detection: UV225nm Carbinoxamine (1.0mg/ml) 0.5µl Cl Tramadol (1.0mg/ml) 3C 3C

8 Compatible with SFC CSMSIL CiRAL columns are compatible with SFC and exhibit similar performance compared to PLC. CSMSIL Application Data CSMSIL CiRAL 3A trans-stilbene oxide (2.0mg/ml) PLC CSMSIL CiRAL 3A Mobile phase: A: C 2 B: 2-Propanol B conc. 10% Flow rate: 3.0 ml/min BPR: 10 MPa Temperature: 40 C SFC trans-stilbene oxide (2.0mg/ml) 2.0µl CSMSIL Application Data CSMSIL CiRAL 3C Detection: UV270nm 1-Phenoxy-2-propanol (1.0mg/ml) 1.5µl PLC CSMSIL CiRAL 3C Mobile phase: A: C 2 B: 2-Propanol B conc. 10% Flow rate: 3.0 ml/min BPR: 10 MPa Temperature: 40 C Detection: UV270nm SFC 1-Phenoxy-2-propanol (1.0mg/ml) 3.0µl rdering Information CSMSIL CiRAL 3 Packed Columns Analytical Columns (Particle Size: 3 μm) Product ame Column Size I.D. x Length (mm) Product umber CSMSIL CiRAL 3A 4.6 x x CSMSIL CiRAL 3B 4.6 x x CSMSIL CiRAL 3C 4.6 x x CSMSIL CiRAL 5 Packed Columns Analytical / Preparative Columns (Particle Size: 5 μm) Product ame Column Size I.D. x Length (mm) Product umber 4.6 x CSMSIL CiRAL 5A 10.0 x x x CSMSIL CiRAL 5B 10.0 x x x CSMSIL CiRAL 5C 10.0 x x * For 10 mm and 20 mm I.D. columns, please inquire about delivery time. For research use only, not intended for diagnostic or drug use.. ijo Karasuma, akagyo-ku, Kyoto JAPA TEL : +81-(0) FAX : +81-(0) Website : info.intl@nacalai.com 1701