Direct optical resolution of vesamicol and a series of benzovesamicol analogues by high-performance liquid chromatography.
The direct optical resolution of the vesicular acetylcholine uptake inhibitors vesamicol and benzovesamicol and nine benzovesamicol analogues were performed by HPLC on a commercially available cellulose tris(3,5-di-methylphenyl carbamate) chiral stationary phase. Separation of each enantiomeric pair was optimized with respect to solvent strength and flow-rate, using mobile phase mixtures of hexane-2-propanol-diethylamine. The method has been successfully applied to the analysis of the optical purity of benzovesamicol intermediates and products, including (-)-5-[123I]iodobenzovesamicol which is currently undergoing clinical evaluation as a tracer for mapping central cholinergic neurons, and the purification of both antipodes of (+/-)-7-[125I]iodobenzovesamicol.
Gildersleeve
D L
DL
Department of Internal Medicine, University of Michigan Medical School, Ann Arbor 48109-0552.
Jung
Y W
YW
Wieland
D M
DM
D015081:2-Naphthylamine / Q000031:analogs & derivatives* / Q000302:isolation & purification; D002482:Cellulose; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D010622:Phencyclidine / Q000031:analogs & derivatives* / Q000302:isolation & purification; D010880:Piperidines / Q000302:isolation & purification*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes
D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D010880:Piperidines; D013764:Tetrahydronaphthalenes; C065043:5-iodobenzovesamicol; C088311:7-iodobenzovesamicol; C006189:vesamicol; D002482:Cellulose; D015081:2-Naphthylamine; D010622:Phencyclidine