TCI Chiral HPLC Column

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TCI Chiral HPLC Column ~ Spiral Polymer New Chiral Stationary Phase ~ Tokyo Chemical Industry Co.,Ltd. Chromatography Department 29 Tokyo Chemical Industry Co., Ltd.

Features of TCI Chiral A unique new stationary phase Polymaleimide spiral polymer and chiral side group coated on Silicagel. Suitable for separating of a wide range compounds Carbonyls (Ketones, Esters, Carboxylic acids, N-Protected Amino acid), Alcohols and others. Performance for both normal phase and reversed phase. Superior column longevity Maximum pressure of 29psi (2MPa) High throughput analysis High column load capacity Affordable price 29 Tokyo Chemical Industry Co., Ltd.

Mechanism of Chiral Recognition 1. Steric recognition of the spiral polymer area 2. Steric recognition of the side group (substituent area) 3. Electrostatic interaction between the analyte and the side group 4. PI-PI and other interactions between the analyte and the side group 29 Tokyo Chemical Industry Co., Ltd.

Suitable Analytes Molecule size pka Typically better separation is obtained for smaller size compounds than for larger size compounds. Ex. MW~4 is better than ~8 Neutral and acidic compounds are more often successfully separated than basic compounds. Recognition, target functional groups 1: Esters, Lactones, Ketones 2: N-protected amino acids, Carboxylic acids 3: Alcohols, Diols, Phenols 4: thers 29 Tokyo Chemical Industry Co., Ltd.

Analytical Condition Normal Phase (Standard starting condition) n-hexane / IPA = 9/1 Elution time is long increase IPA ratio (ex.3%) Elution time is short decrease IPA ratio (ex.1%) Acidic analyte add.1% of Trifluoroacetic acid Basic analyte add.1% of Diethylamine Reversed Phase (Standard starting condition) Acetonitrile / Water = 2/8 Elution time is long increase acetonitrile ratio (ex.4%) Elution time is short decrease acetonitrile ratio (ex.1%) Acidic analyte add.1% of Trifluoroacetic acid Basic analyte choice buffer solution Non-usable solvents THF, Toluene, Halogenated solvents (Chloroform, etc.) 29 Tokyo Chemical Industry Co., Ltd.

N TCI Chiral Product Line TCI Chiral MB-S TCI Chiral BP-S TCI Chiral CH-S Column N N N N N Particle size 3μm, μm 3μm, μm 3μm, μm Retention Power (Normal Phase) Analyte High Medium Weak Carbonyl (Ketones, Esters, Carbonyl (Ketones, Esters, Carbonyl (Ketones, Esters, Lactones, Carboxylic Lactones, Carboxylic Lactones, Carboxylic acids, acids, Amides, Lactams, acids, Amides, Lactams), Amides, Lactams, Amino Amino acid derivatives), mono-alcohols, acid derivatives), mono-alcohols, Diols, Diols, Ethers, Epoxides, Diols, Ethers, Epoxides, Sulfoxides Heterocycles Heterocycles, Sulfoxides 29 Tokyo Chemical Industry Co., Ltd.

Stability Test Column : uv TCI Chiral BP-S Column Size : 4.6mmID mm 2 Mobile Phase : Hexane/IPA = 9/1 Detection : UV 4 nm 2 Flow Rate :.7 ml/min Temperature : 4 Sample : Benzoin 17 injection α Rs 1 2.13 2.41 4 2.14 2.3 6 2.13 2.32 8 2.12 2.3 1 2.12 2.29 1 Injection:1 1 Injection:4 1 Injection:6 7 Injection:8 Injection:1.. 1. 1. 2. 2. 3. 3. 4. 4. min 29 Tokyo Chemical Industry Co., Ltd.

Batch to Batch Reproducibility alpha 2. 2 1. 1 Benzoin 1-Phenyl-1,2- ethandiol. 1st 2nd 3rd 4th th 6th 7th TCI Chiral MB-S (3μm) 29 Tokyo Chemical Industry Co., Ltd.

High Throughput Screening Column : TCI Chiral MB-S (3μm) Mobile Phase : Hexane/IPA = 9/1 Detection : UV 4 nm Temperature : 4 Sample : Benzyl DL-Mandelate It is possible to do one minute screening Using a short column and high flow rate. mv.. 22. 2. 17. 4.6mmID mm Flow Rate: 1.mL/min 22. 2. 17. 4.6mmID mm Flow Rate:.mL/min 1. 1. 12. 12. 1. 1. 7. 7... 2. 2.... 2.. 7. 1. 12. min.. 1. 1. 2. 29 Tokyo Chemical Industry Co., Ltd.

Column Load Capacity Test Analysis 12. 1. 7.. 2.. 2 1 2 3 4 min Column Size : 4.6mmI.D. mm Flow Rate : 1. ml/min Sample Load:.mg 1 2 3 4 Time(min) Load Capacity Test Analysis column Column Size : 4.6mmI.D. mm Flow Rate : 1. ml/min N-Cbz-proline Column Mobile Phase Temperature : 4ºC Detection : UV4nm Load Capacity Test Prep column N H : TCI Chiral MB-S (µm) : n-hexane/2-propanol/tfa =9/1/.1 Column Size : 2.mmI.D. mm Flow Rate : 9. ml/min 1 1 Sample Load: 2mg Sample Load: 4mg 1 2 3 4 min 1 2 3 4 Time(min). 2. 4. 6. 8. 1. 12. 14. 3 6 9 12 Time(min) 29 Tokyo Chemical Industry Co., Ltd.

Normal and Reversed Phase Application Column Size : 4.6mmID mm Detection : UV21nm Flow Rate : 1.mL/min Temperature : 4 H Butyl Lactate mv Normal Phase : Hexane/IPA=7/3(MB-S), 8 9/1(BP-S and CH-S) 3 6 7 6 2 1 1 MB-S 4 3 2 BP-S 4 3 2 CH-S 1 1. 2.. 7. min. 2.. 7. min. 2.. 7. min Reversed Phase : Acetonitrile/Water=1/9 3 3 2 1 1 MB-S 3 2 1 1 BP-S 1. 7.. 2. CH-S.. 1. 1. min.. 1. 1. min... 1. 1. min 29 Tokyo Chemical Industry Co., Ltd.

Normal and Reversed Phase Application Column Size : 4.6mmID mm Detection : UV21nm Flow Rate : 1.mL/min Temperature : 4 Normal Phase : Hexane/IPA=9/1 6 Glycidyl Butyrate 2 2 4 MB-S 2 1 BP-S 17 1 1 CH-S 3 2 1 1 7 1.. 1. 1. 2.. min.. 1. 1. min.. 1. 1. min 17. 1. Reversed Phase : Acetonitrile/Water=1/9 3 3 1 9 8 12. 1. 7. MB-S 2 1 BP-S 7 6 4 CH-S. 2. 1 3 2 1... 1. 1. 2.. min.. 1. 1. 2.. min.. 1. 1. 2.. min 29 Tokyo Chemical Industry Co., Ltd.

N-Protected Alanine Application N-Acetyl N-BC N-CBZ N-FMC Alpha 1.9 1.7 2.6 3.3 Rs 8.9 2.4 11. 13. 8 7 6 4 3 N-Acetyl alanine 1 1 7 Column : TCI Chiral BP-S (μm) Column Size : 4.6mmID mm Mobile Phase : Hexane/IPA/TFA=9//.1 Detection : UV21nm (N-Acetyl, N-BC) UV4nm (N-CBZ, N-FMC) Flow Rate : 1.mL/min Temperature : 4 N-BC alanine 2 1.. 1. 1. 2.. min 2. 2.. 7. min 1 1 N-CBZ alanine 2 1 1 N-FMC alanine 1 2 3 4 min.. 1. 1. 2.. min 29 Tokyo Chemical Industry Co., Ltd.

TCI Chiral and Natural Polymer Application Comparison Carvone 1,4-Di--benzylthreitol 3 2 1 1 4 4 3 3 2 1 4 4 3 3 2 1 H H CH 2 CH 2 Ph H H 12. 1. CH 2 CH 7. 2 Ph. 1 1 2.. 2.. 7. min 4 4 3 TCI Chiral MB-S. 2.. 7. min 7 6 Amylose type 1. 2.. 7. min TCI Chiral MB-S 9 8 7. 3 3 1 2 3 4 min Amylose type 1 3 6 4 2 2 1 1. 2.. 7. min TCI Chiral BP-S 3 2 1 Amylose type 2. 2.. 7. min 4 3 2 1 9. 2.. 7. min TCI Chiral BP-S 1 1 9 1 2 3 4 min Amylose type 2 4 7 8 8 3 6 7 7 3 2 1 4 3 6 4 3 6 4 3 1 2 2 2 1 1 1 TCI Chiral CH-S. 2.. 7. min Cellulose type. 2.. 7. min. 2.. 7. min TCI Chiral CH-S 1 2 3 4 min Cellulose type 29 Tokyo Chemical Industry Co., Ltd.

4 4 3 3 2 1 1 9 8 7 6 4 3 2 1 8 7 6 4 3 2 1.. 1. 1. min.. 1. 1. min 9.. 1. 1. min TCI Chiral and Natural Polymer Application Comparison Guaiacol Glycerol Ether 2 1 1 4 3 2 1 22. 2. 17. 1. 12. 1. 7.. 2.. H H.. 1. 1. min 6.. 1. 1. min 1 2 3 4 min 7.. 2.. 1. 12. 1. 7.. 2.. 1. 7.. 2.. -2. -. 1 2 3 4 min.. 1. 1. 2.. min Mevalonolactone.. 1. 1. min 3. 3. 2. 2. 1... 4 3 2 1-1 -2-3 22. 2. 17. 1. 12. 1. 7.. 2.. -2... 1. 1. 2.. min TCI Chiral MB-S Amylose type 1 TCI Chiral MB-S Amylose type 1 H 1... 1. 1. 2.. min TCI Chiral BP-S Amylose type 2 TCI Chiral BP-S Amylose type 2.. 1. 1. 2.. min TCI Chiral CH-S Cellulose type TCI Chiral CH-S Cellulose type 29 Tokyo Chemical Industry Co., Ltd.

TCI Chiral and Natural Polymer Application Comparison 2 1 1 Butyl Lactate H 1. 12. 1. 7.. 2. 17. 1. 12. 1. 7.. 2. Glycidyl p-toluenesulfonate S 3 3 2 1 1. 2.. 7. min 3. 2.. 7. min 3 2 1 1. 2.. 7. min... 2.. 7. min.. 1. 1. 2.. min.. 1. 1. 2.. min TCI Chiral MB-S Amylose type 1 TCI Chiral MB-S Amylose type 1 3 4 8 3 7 4 3 6 2 3 1 2 2 4 1 3 1 1 1 2 1. 2.. 7. min 6 4 3 2 1. 2.. 7. min 4.. 1. 1. 2.. min.. 1. 1. 2.. min 9 8 7 7 6 6 4 4 3 3 2 2 1 1.. 1. 1. 2.. min TCI Chiral BP-S Amylose type 2 TCI Chiral BP-S Amylose type 2.. 1. 1. 2.. min TCI Chiral CH-S Cellulose type TCI Chiral CH-S Cellulose type 29 Tokyo Chemical Industry Co., Ltd.

TCI Chiral and Natural Polymer Application Comparison 1 1 1 7 1 2-Chloropropionic Acid Cl. 2.. 7. min TCI Chiral MB-S 7 H. 2.. 7. min 9 Amylose type 1 2 2 17 1 1 1 7 4-Isopropyl-3-propionyl-2- oxazolidinone 1 2 3 4 min TCI Chiral MB-S 9 8 7 6 N 4 3 2 1. 2.. 7. min Amylose type 1 1 1 7 8 7 6 4 3 1 7 1 7 2 1. 2.. 7. min TCI Chiral BP-S -1. 2.. 7. min 1 Amylose type 2. 2.. 7. min TCI Chiral BP-S. 2.. 7. min Amylose type 2 1 1 1 1 1 7 7 7 7 -. 2.. 7. min TCI Chiral CH-S -.. 1. 1. min Cellulose type. 2.. 7. min TCI Chiral CH-S. 2.. 7. min Cellulose type 29 Tokyo Chemical Industry Co., Ltd.

SFC Application CH C CH 2 H Benzyl DL-Mandelate 1. 2.. 3. Time(min.) Column : TCI Chiral MB-S (3µm) Column Size : 4.6mmID 1mm Temperature : 4ºC Pressure : 2MPa Mobile Phase : C 2 /IPA=9/1 Detection : UV4nm Flow Rate : 2.mL/min Sample : Benzyl DL-Mandelate.99mg/mL(IPA) Injection Vol. : µl Column Pressure: 2.4MPa SFC : Supercritical Fluid Chromatography 29 Tokyo Chemical Industry Co., Ltd.

Complete TCI Chiral Product Line Column Type TCI Chiral MB-S TCI Chiral BP-S TCI Chiral CH-S Particle Size 3μm μm 3μm μm 3μm μm 4.6mm mm S381 S384 S38 S38 S383 S386 4.6mm 1mm S381 S384 S382 S38 S383 S386 4.6mm mm S3811 S3841 S3821 S381 S3831 S3861 Cartridge type guard for 4.6mm S3849(1/Pack) S389(1/Pack) S3869(1/Pack) column (3.mm 1mm) 2.mm mm S3816 S3846 S3826 S386 S3836 S3866 2.mm 1mm S3812 S3842 S3822 S382 S3832 S3862 2.mm mm S3813 S3843 S3823 S383 S3833 S3663 Guard for 2. (or 4.6mm ) Column (1.mm 1mm ) S3819(3/Pack) S3829(3/Pack) S3839(3/Pack) 1.mm mm - S387 - S388 - S389 2.mm mm - S3871 - S3881 - S3891 3.mm 1mm guard column is a cartridge type column and needs a holder. Holder:S14 29 Tokyo Chemical Industry Co., Ltd.

Guard Column For 4.6mmID column Cartridge type guard column Size : 3mm 1mm For 2.mmID column or clean sample analysis Size : 1mm 1mm Holder Connector Guard Column Main Column 29 Tokyo Chemical Industry Co., Ltd.

Compounds of Application 1 29 Tokyo Chemical Industry Co., Ltd.

Compounds of Application 2 29 Tokyo Chemical Industry Co., Ltd.