Direct enantiomeric separation of platelet-activating factor receptor antagonist SM-10661 by ligand-exchange high-performance liquid chromatography with a copper (II) N,S-dioctyl-D-penicillamine complex.
The enantiomeric separation of SM-10661, a platelet activating factor receptor antagonist, was investigated by HPLC using ligand-exchange chiral stationary phases. The stereoisomers of SM-10661 could all be separated by ligand-exchange HPLC with a Cu(II) N,S-dioctyl-D-penicillamine complex (Sumichiral OA-5000). The mechanism for the resolution includes the involvement of hydrophobic interactions between SM-10661 and Cu(II) D-penicillamine.
Okamoto
M
M
Environmental Health Science Laboratory, Sumitomo Chemical Co., Ltd., Osaka, Japan.
Ueda
Y
Y
Takahashi
K
K
Nakazawa
H
H
Doi
T
T
D002412:Cations; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003300:Copper / Q000737:chemistry*; D007536:Isomerism; D010396:Penicillamine / Q000737:chemistry*; D010980:Platelet Membrane Glycoproteins / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D011956:Receptors, Cell Surface; D043562:Receptors, G-Protein-Coupled; D013844:Thiazoles / Q000737:chemistry*; D053778:Thiazolidines
D002412:Cations; D010980:Platelet Membrane Glycoproteins; D011956:Receptors, Cell Surface; D043562:Receptors, G-Protein-Coupled; D013844:Thiazoles; D053778:Thiazolidines; C039351:platelet activating factor receptor; C065776:3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one; D003300:Copper; D010396:Penicillamine