18Handling Products
Sumika Chemical Analysis Service, Ltd.

SUMICHIRAL OA ------------------------------------172-176

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Chiral columns for enantiomer separation by HPLC
[SUMICHIRAL OA] *SUMICHIRAL is a trademark of Sumika Chemical Analysis Service, Ltd.
SUMICHIRAL OA columns are high-performance chiral columns for enantiomer separation by HPLC. On SUMICHIRAL OA
columns direct separation of various enantiomers can be realized effectively. Enantiomeric separation is achieved from the various
diastereomeric interactions such as hydrogen bonding, charge transfer and host-guest interactions, etc.
SUMICHIRAL OA columns are very useful for the accurate determination of the optical purity and for the preparation of pureenantiomers of biologically active compounds such as pharmaceuticals, pesticides, and perfumes.
Improved Pirkle Type
Ligand exchange Type
Host-guest TypeSUMICHIRAL OA
Standard type
SUMICHIRAL

Chiral component

Inverted type
SUMICHIRAL

Mode ＊＊

OA-2000(R)-phenylglycine

OA-2000S

OA-2500(R)-1-naphthylglycine

OA-2500SNPRP

OA-3100(S)-valine

OA-3100R

NP,RP

OA-3200(S)-tert-leucineOA-3200R

NP,RP

OA-3300(R)-phenylglycine

OA-3300S

NP,RP

OA-4000(S)-valine (S)-1-(α-naphthyl)ethylamine

OA-4000RNP

OA-4100(S)-valine (R)-1-(α-naphthyl)ethylamine

OA-4100R

NP

OA-4400(S)-proline (S)-1-(α-naphthyl)ethylamine

OA-4400RNP

OA-4500(S)-proline (R)-1-(α-naphthyl)ethylamine

OA-4500RNP

OA-4600(S)-tert-leucine (S)-1-(α-naphthyl)ethylamine

OA-4600R

NP

OA-4700(S)-tert-leucine (R)-1-(α-naphthyl)ethylamine

OA-4700RNP

OA-4800(S)-indoline-2-carboxylic acid (S)-1-(α-naphthyl)ethylamine＊NP

OA-4900(S)-indoline-2-carboxylic acid (R)-1-(α-naphthyl)ethylamine＊

NP

OA-5000(D)-penicillamine

OA-5000L

RP

OA-6000(L)-tartaric acid (R)-1-(α-naphthyl)ethylamine

OA-6000R

RP

OA-6100(L)-tartaric acid, (S)-valine (S)-1-(α-naphthyl)ethylamine

OA-6100R

RP

OA-7000

β-cyclodextrin with novel spacer＊

RP

OA-7100

β-cyclodextrin＊

RP

OA-7500

methyl-β-cyclodextrin＊

RP

OA-7600

methyl-α-cyclodextrin＊

RP

OA-7700

acetyl-β-cyclodextrin with novel spacer＊

RP

OA-8000chiral pseudo-18-crown-6-ether＊NP,RP

Most popular phases＊Enantiomeric stationary phases (inverted types) are available with the exception of OA-4800, 4900, 7000 series and 8000. On these phases, the elution orderof enantiomer is inverted.
＊＊NP : normal-phase mode, RP : reversed-phase modeStandard column dimensions

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Guard column

・4.0 × 10 mm

Analytical column

・4.6 × 250 mm
4.6 × 150 mm is also available for OA-8000.
・4.6 × 150 mm (for OA-5000, 6000, 6100)
4.6 × 50 mm is also available for OA-5000.

Preparative column

・8.0 × 250 mm, 10 × 250 mm, 20 × 250 mm

Special Merits of SUMICHIRAL OA● The large number of theoretical plates of the columns offers high resolution.
● The packing materials have chemical stability and the columns have long life.
● The enantiomeric stationary phases give the inverse elution orders, resulting in accurate determination of the optical purity andefficient preparation of the enantiomer are attained.

Improved Pirkle Type 1■ Amide Type: Asymmetric carbon atoms are bonded directly with CONH group
OA-2000 series have a 3,5-dinitrobenzoyl group as the π-acid and may interact with the solute molecule by charge transfer, hydrogenbonding, etc. The enantiomers of aromatic compounds, esters, carboxylic acids and alcohols may be directly separated on OA-2000
series. OA-2000 is especially effective for pyrethroidal esters, OA-2500 for carboxylic acids such as profen-drugs.

SUMICHIRAL OA-2000 series<Pesticide><Profen-drugs>

Fenvalerate

Ketoprofen

Naproxen

Column: SUMICHIRAL OA-2000 (250×4.6 mm)
Mobile phase : hexane/1,2-dichloroethane/ethanol		(500/30/0.15)
Flow rate: 1.0 mL/min
Detection: UV at 230 nmColumn: SUMICHIRAL OA-2500 (250×4.6 mm)
Mobile phase : 0.03 mol/L ammonium acetate in		methanol
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-2500 (250×4.6 mm)
Mobile phase : 0.05 mol/L ammonium acetate in		methanol
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

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Improved Pirkle Type 1■ Urea Type: Asymmetric carbon atoms are bonded directly with NHCONH group
OA-3000 series have 3,5-dinitrophenylurea group as the π-acid and, in the reverse phase mode, promote chiral discrimination bycharge transfer, hydrogen bonding, etc. In general OA-3000 series are effective for carboxylic acids, and especially for acetyl- andurethane-amino acids, as well as dansylamino acids. OA-3300 offers good direct separation for profen-drugs, acetyl-amino acids,BOC-amino acids and benzyl-amino acids.

SUMICHIRAL OA-3000 series<Amino acid N-derivatives><Atropisomer>

BOC-Phenylalanine

Dansyl-Valine

1,1'-BinaphtholColumn: SUMICHIRAL OA-3300 (250×4.6 mm)
Mobile phase : 0.01 mol/L ammonium acetate in		methanol
Flow rate: 0.6 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-3200 (250×4.6 mm)
Mobile phase : 0.01 mol/L ammonium acetate in		methanol
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-3300 (250×4.6 mm)
Mobile phase : hexane/2-propanol/methanol		(70/20/10)
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

Improved Pirkle Type 2■ Two chiral centers at amine and amino acid are bonded with NHCONH group
OA-4000 series have a naphthyl group as the π-base, and two chiral centers at amine and amino acid group. By charge transfer,hydrogen bonding, etc., chiral discrimination is acheived, and a wide variety of compounds such as pharmaceuticals of amine andamino alcohols, alcohols, esters and amides can be directly resolved in the normal phase mode. Amide and urethane derivatives ofamines, alcohols, etc. can be resolved effectively.

SUMICHIRAL OA-4000 series<Amine-type drugs>

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Tolperizone

Isoproterenol

Chlormezanone

Column: SUMICHIRAL OA-4500 (250×4.6 mm)
Mobile phase : hexane/tetrahydrofuran/methanol/		 triﬂuoroacetic acid (60/35/5/0.2)
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-4900 (250×4.6 mm)
Mobile phase :	hexane/1,2-dichloroethane/methanol/		 triﬂuoroacetic acid (240/140/20/1)
Flow rate: 1.0 mL/min
Detection: UV at 280 nm

Column: SUMICHIRAL OA-4700 (250×4.6 mm)
Mobile phase : hexane/2-propanol/methanol/		 triﬂuoroacetic acid (80/15/5/0.2)
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

Ligand exchange Type■ The chiral components are coated hydrophobically on ODS
OA-5000 and 6000 series offer chiral discrimination by ligand exchange interaction in the reversed phase mode. The chiral ligands
such as penicillamine (OA-5000) or tartaric acid derivatives (OA-6000 series) are coated on ODS silica, though the volume of organic
solvents added to the mobile phase is limited. Mobile phases including Cu++ ions are used in these columns.
They are effective for direct enantiomer separation of not only amino acids or hydroxy acids but also copper-chelate forming
compounds such as amino alcohols, diamines, dicarboxylic acids, aminolactames and dipeptides. Especially OA-5000 can be appliedfor extremely wide range, while OA-6100 is effective forβ-amino acids,β-hydroxy acids and hydrophilic amin acids.

SUMICHIRAL OA-5000, OA-6000 series<Amino acids>
Tryptophan

ValineBaclofen

Column: SUMICHIRAL OA-6100 (150×4.6 mm)
Mobile phase : 2 mmol/L copper(Ⅱ) sulfate in [water/		 acetonitrile (90/10)]
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-5000 (150×4.6 mm)
Mobile phase : 2 mmol/L copper(Ⅱ) sulfate in [water/		 2-propanol (95/5)]
Flow rate: 1.0 mL/min
Detection: UV at 254 nmColumn: SUMICHIRAL OA-5000 (150×4.6 mm)
Mobile phase : 2 mmol/L copper(Ⅱ) sulfate in [water/		 2-propanol (85/15)]
Flow rate: 1.0 mL/min
Detection: UV at 254 nm<Hydroxy acids>(Inversion of elution order)

Mandelic acid

Lactic acid

Lactic acid

Column: SUMICHIRAL OA-6100 (150×4.6 mm)
Mobile phase : 2 mmol/L copper(Ⅱ) sulfate in [water/		 acetonitrile (90/10)]
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-5000 (150×4.6 mm)
Mobile phase :	2 mmol/L copper(Ⅱ) sulfate in [water/		 acetonitrile (95/5)]
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-5000L (150×4.6 mm)
Mobile phase : 2 mmol/L copper(Ⅱ) sulfate in [water/		 acetonitrile (95/5)]
Flow rate: 1.0 mL/min
Detection: UV at 254 nm

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Host-Guest Type■ Cyclodextrin bonded chiral stationary phase with novel spacer
OA-7000 is a novel chiral stationary phase withβ-cyclodextrin bonded to the silica gel via a new type of spacer. A large number ofracemates, including ketones, amines and amino acid derivatives can be separated under reversed phase conditions.
(1) Sharp peaks and high theoretical plate numbers are obtained.
Improved peak shape is due to the effect of hydrophilic spacer moiety which prevents secondary interactions between the silica
gel and the sample molecules.
(2) Popular reversed phase conditions can be used.

■ Novel Chiral Stationary phase bonded with crown ether
OA-8000 is a novel chiral stationary phase bonded with chiral crown ether to aminopropyl silica gel. This is very effective forenantiomer separations of amines, aminoalcohols and amino acids, especially for hydrophobic amines.
(1) Stationary phase is covalent bond type and very stable.
(2) Both reversed and normal phases can be used.
(3) Sharp peaks and high theoretical plate numbers are obtained.

SUMICHIRAL OA-7000, OA-8000 series<Aromatic compounds>
Flavanone

Cyclopentolate

Chlorthalidone

Column: SUMICHIRAL OA-7000 (250×4.6 mm)
Mobile phase : 20 mmol/L phosphate buffer (pH 2.0)/		 acetonitrile (60:40)
Flow rate: 0.85 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-7000 (250×4.6 mm)
Mobile phase :	20 mmol/L phosphate buffer (pH 3.0)/		 acetonitrile (60:40)
Flow rate: 0.2 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-7000 (250×4.6 mm)
Mobile phase : 20 mmol/L phosphate buffer (pH 3.0)/		 acetonitrile (80:20)
Flow rate: 0.7 mL/min
Detection: UV at 254 nm<Primary amine and aminoalcohol>

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1-(1-Naphthyl)-ethylamine

Phenylpropanolamine

Cysteine

Column: SUMICHIRAL OA-8000 (250×4.6 mm)
Mobile phase : perchloric acid in water (pH 2.0)/		 acetonitrile (70/30)
Flow rate: 0.7 mL/minDetection: UV at 254 nm

Column: SUMICHIRAL OA-8000 (250×4.6 mm)
Mobile phase : hexane/ethanol/triﬂuoroacetic acid		(70/30/0.5)
Flow rate: 0.7 mL/min
Detection: UV at 254 nm

Column: SUMICHIRAL OA-8000 (250×4.6 mm)
Mobile phase : hexane/ethanol/triﬂuoroacetic acid		(70/30/0.5)
Flow rate: 0.7 mL/min
Detection: UV at 254 nm