6 Optical Isomer Separation Columns

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1 YMC GENERAL CATALG ptical Isomer Separation Columns YMC CHIRAL CD BR series YMC CHIRAL NEA YMC CHIRAL PREP CD ST/PM 128,129 13, , 第章.indd :57:24 AM

ptical isomer structural isomer YMC CHIRAL CD BR series Cyclodextrin type optical isomer separation column Useful for separation of optical isomers and structural isomers Three cavity types, α, β and

columns. Each column possesses α-, β- or γ-bromo-cyclodextrin as a functional group. Selection from the 3 types of columns enables analysis of a wide range of compounds.

2 ptical isomer structural isomer YMC CHIRAL CD BR series Cyclodextrin type optical isomer separation column Useful for separation of optical isomers and structural isomers Three cavity types, α, β and γ, are available Particle size:5 µm Pore size:12 Å Usable ph range:3.5.5 p t i c a l i s o m e r s e p a r a t i o n c o l u m n u t i l i z i n g h o s t - g u e s t i n t e r a c t i o n YMC CHIRAL CD BR series is composed of 3 types of optical isomer separation columns. Each column possesses α-, β- or γ-bromo-cyclodextrin as a functional group. Selection from the 3 types of columns enables analysis of a wide range of compounds. In addition, YMC CHIRAL CD BR series shows different selectivity from DS because the separation is based on host-guest interaction. YMC CHIRAL CD BR series is useful for separating structural isomers that are difficult to separate on DS. For separation of structural isomers N 2 m o N 2 N 2 o m -Estradiol -Estradiol p p min min 2 4 min Column : YMC CHIRAL α-cd BR Eluent :.1 M C-CNa (ph 4.)/ methanol (9/1) Column : YMC CHIRAL β-cd BR Eluent :methanol/water (2/8) Column : YMC CHIRAL γ-cd BR Eluent :methanol/water (5/5) Temperature :3 Detection :UV at 23 nm α-cd BR, β-cd BR and γ-cd BR show different separation characteristics since they have different cavity sizes. Selection from the 3 types of columns according to the characteristics of analytes enables analysis of a wide range of compounds. These columns are useful for coupling with DS columns. 128 第章.indd :57:29 AM

3 For separation of optical isomers C CH- CI N N F CH-C CH min Column : YMC CHIRAL β-cd BR Eluent :.5 M triethylamine-acetic acid (ph 4.)/ acetonitrile (1/9) 1 2 min Column : YMC CHIRAL β-cd BR Eluent :.5 M triethylamine-acetic acid (ph 5.4)/ acetonitrile (95/5) min Column : YMC CHIRAL γ-cd BR Eluent :.5 M triethylamine-acetic acid (ph 4.)/ acetonitrile (/4) Since cyclodextrin is a chiral compound, various optical isomers can be separated well with YMC CHIRAL CD BR series columns. YMC CHIRAL CD BR series is useful as optical isomer separation columns that can be used with a reversed-phase mobile phase. rdering information Analytical columns Packing material Particle size Pore size (µm) (Å) α-cd BR S-5 12 β-cd BR S-5 12 γ-cd BR S DA12S5-154WT DA12S5-254WT DB12S5-154WT DB12S5-254WT DG12S5-154WT DG12S5-254WT Guard cartridge columns (three-pack) Packing material Particle size Pore size (µm) (Å) α-cd BR S DA12S5-G34CC β-cd BR S DB12S5-G34CC γ-cd BR S DG12S5-G34CC A cartridge holder will need to be purchased separately before using this product for the first time. Cartridge holder Cartridge holder (inner diameter: 4. mm) XPCHW 129 第章.indd :57:31 AM

4 ptical isomer YMC CHIRAL NEA(R),(S) Synthesized macromolecule-type chiral column Elution order can be reversed by selection (R) or (S) Can be used in both normal-phase and reversedphase Useful for preparative separation Available for bulk scale Excellent cost performance Particle size:5 µm Pore size:3 Å Usable ph range:2..5 C h i r a l p o l y m e r - b o n d e d s i l i c a g e l f o r o p t i c a l i s o m e r s e p a r a t i o n YMC CHIRAL NEA (R) and (S) are chiral polymerbonded silica gel for optical isomer separation. Chiral discrimination is based on the higher-order structure of chiral macromolecules, which includes hydrogen bonding, π-π interaction, hydrophobic interaction, etc. YMC CHIRAL NEA (R) and (S) have excellent durability and cost performance. Used with a reversed-phase mobile phase Ketamine NH CI 1 2 min Column : YMC CHIRAL NEA (R) Eluent :acetonitrile/.5 M NaCI4 (4/) Detection :UV at 28 nm (S) (R) 2,2,2-Trifluoro-1-(9-anthryl)ethanol min Used with a normal-phase mobile phase (S) (R) CF 3 CH Column : YMC CHIRAL NEA (R) Eluent :acetonitrile/water (4/) Temperature :3 2,2,2-Trifluoro-1-(9-anthryl)ethanol CF 3 CH Durability 1 2 min Column : YMC CHIRAL NEA (R) Eluent :hexane/ethanol (98/2) Temparature :3 N,7 1.1 N, Flow conditions Column :YMC CHIRAL NEA (R) Eluent :acetonitrile/.5 M NaCI4 (4/) Time :1 hours 1 2 min 1 2 min Measurement conditions Eluent :acetonitrile/.5 M NaCI4 (4/) Sample :Propranolol 13 第章.indd :57:35 AM

5 Example for preparative separation of optical isomers Excellent scalability Column: YMC CHIRAL NEA (R) analytical column preparative column () () 1,1' Bi-2-naphthol optical purity :> 99% recovery :> 99% collection :1 mg optical purity :> 99% recovery :> 99% collection :1 mg Performance/1 µm, 25 2 mmi.d : 254. mmi.d. () loading :> 2 mg/cycle purity :> 99% recovery :> 99% purification capacity :> mg/hour Loading Study () () () : 252 mmi.d. Large-scale separation immediately feasible, if separable with an analytical column. Above is a separation data using 1 µm NEA. YMC can supply 1 µm NEA packing material in order to comply with bench scale to production scale. This packing material can be supplied in bulk for Dynamic Axial Columns or as packed columns. Please contact us for further informations about test columns, bulk supply, etc. rdering information Analytical columns for reversed-phase Packing material Particle size Pore size (µm) (Å) NEA (R) S-5 3 NEA (S) S NR3S5-154WT NR3S5-254WT NS3S5-154WT NS3S5-254WT Analytical columns for normal-phase NEA (R) S-5 3 NEA (S) S CR3S5-154WT CR3S5-254WT CS3S5-154WT CS3S5-254WT Guard cartridge columns (three-pack) for reversed-phase Packing material Particle size Pore size (µm) (Å) NEA (R) S NR3S5-G34CC NEA (S) S NS3S5-G34CC Guard cartridge columns (three-pack) for normal-phase NEA (R) S CR3S5-G34CC NEA (S) S CS3S5-G34CC A cartridge holder will need to be purchased separately before using this product for the first time. Cartridge holder Cartridge holder (inner diameter: 4. mm) XPCHW 131 第章.indd :57:37 AM

6 ptical isomer YMC CHIRAL PREP CD ST / YMC CHIRAL PREP CD PM β-cyclodextrin modified silica gel packing material Can separate various optical isomers Can be used in both normal-phase and reversed-phase modes Various particle sizes are available Bulk supply at kilogram scale is available Excellent cost performance Applicable to large-scale isolation by simulated moving bed (SMB) chromatography Particle size:1 µm, 2 µm, 5 µm Pore size:12 Å Usable ph range:2. 7. Packing material for preparative isolation of optical isomers with excellent cost performance YMC CHIRAL PREP CD ST / PM are suitable packing materials for preparative isolation of optical isomers. ST is suitable for use mainly in reversed-phase mode, while PM can be used in both normal-phase and reversed-phase modes. The cost is considerably less than that of the conventional packing materials for optical isomers. Therefore YMC CHIRAL PREP CD ST / PM are appropriate not only for semi-preparative isolation, but also for industrial isolation. They are also applicable to simulated moving bed (SMB) chromatography and axial compression columns. For preparative isolation of optical isomers S2NH2 NH CI Chlorthalidone ptical Purity :> 99.9% Recovery :94.8% Collection :47.4 mg ptical Purity :> 95.7% Recovery :97.9% Collection :49. mg 1 mg ( mmi.d. 2 mmi.d. ) 2 ( 1 mm ) 25 mm F1 F min min Column:YMC CHIRAL PREP CD ST (1 µm, 12 Å) Scale up from analytical to preparative conditions is fast and easy with high sample loading. F1 Collection 171 g/cyc F2 Collection 177 g/cyc rdering information Analytical columns Packing material ST Particle size (µm) Pore size (Å) S ST12S11-254WT PM PM12S11-254WT Packing material Packing material YMC CHIRAL PREP CD ST YMC CHIRAL PREP CD PM Particle size (µm) Pore size (Å) 1 ST12S11 2 ST12S21 5 ST12S PM12S11 2 PM12S21 5 PM12S5 132 第章.indd :57:4 AM

7 High isolation performance Preparation examples CHCH2NH2 NH S 2NH 2 CI S S N CH 2 CH 2 N CHCH2NHCH 1. Norphenylephrine 2. Chlorthalidone 3. Thioridazine 4. Isoproterenol optical isomer Column loading* optical purity (F1) collection (F1) recovery (F1) 1. PM 1 mg > 99.9% 49. mg 99.2% 2. ST 1 mg > 99.9% 47.4 mg 94.8% Highly pure optical isomers can be obtained with high recovery. 3. ST 1 mg > 99.9% 38.5 mg 77.% 4. PM 2 mg > 99.9% 9.5 mg 9.5% 4. PM 25 mg > 99.9% mg 91.3% * : 25 2 mmi.d. (1 µm, 12 Å) Can be used in both normal-phase and reversed-phase modes Normal-phase mode Reversed-phase mode CHCH2NHC Flavanone Terbutaline In addition to water, alcohol, and acetonitrile, hexane or tetrahydrofuran can be used as mobile phase min min Column :YMC CHIRAL PREP CD PM (1 µm, 12 Å) Eluent :hexane/ethanol (95/5) Flow rate :.5 ml/min Injection :5 µl (1 mg/ml) Column :YMC CHIRAL PREP CD ST (1 µm, 12 Å) Eluent :2 mm KH2P4 (ph 4.)/acetonitrile (99/1) Detection :UV at 22 nm Injection :5 µl (1 mg/ml) 133 第章.indd :57:41 AM

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Optical Isomer Separation Columns and Packing Materials

Optical Isomer Separation Columns and Packing Materials 02 Optical Isomer Separation s and Packing Materials CHIRAL ART----------------------------------- 26~29 YMC CHIRAL NEA (R), (S)-----------------------30 YMC CHIRAL CD BR------------------------------31