title: Semipreparative enantiomeric separation of a series of putative melatonin receptor agents using tri-acetylcellulose as chiral stationary phase.
abstract: In order to obtain milligram amounts of the enantiomers of a series of compounds to be tested for binding to the melatonin binding site, a system for semipreparative enantiomeric separation was set up using tri-acetylcellulose as the chiral stationary phase. Interactions of this class of compounds with tri-acetylcellulose were examined on an analytical scale with a series of 20 compounds. Apparently, both steric and electrostatic interactions determine retention behavior on tri-acetylcellulose. Semipreparative separations were carried out for a subset of seven compounds. The purity of the first eluting enantiomer usually was around 99%, whereas the purity of the second eluting enantiomer was slightly less. The system described is easy to use and has the major advantage that a series of compounds can be separated with one technique. The purities obtained are sufficient for a first screen of their affinity.
authors.affiliation: Department of Medicinal Chemistry, University Centre for Pharmacy, University of Groningen, The Netherlands.
authors.forename: J M
authors.initials: JM
authors.lastname: Jansen
authors.forename: S
authors.initials: S
authors.lastname: Copinga
authors.forename: G
authors.initials: G
authors.lastname: Gruppen
authors.forename: R
authors.initials: R
authors.lastname: Isaksson
authors.forename: D T
authors.initials: DT
authors.lastname: Witte
authors.forename: C J
authors.initials: CJ
authors.lastname: Grol
mesh_terms: D001665:Binding Sites; D002482:Cellulose / Q000031:analogs & derivatives*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D007202:Indicators and Reagents; D008550:Melatonin / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism*; D011956:Receptors, Cell Surface / Q000378:metabolism*; D044094:Receptors, Melatonin; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D007202:Indicators and Reagents; D011956:Receptors, Cell Surface; D044094:Receptors, Melatonin; D002482:Cellulose; C024671:cellulose triacetate; D008550:Melatonin