Semipreparative enantiomeric separation of a series of putative melatonin receptor agents using tri-acetylcellulose as chiral stationary phase.
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.
Jansen
J M
JM
Department of Medicinal Chemistry, University Centre for Pharmacy, University of Groningen, The Netherlands.
Copinga
S
S
Gruppen
G
G
Isaksson
R
R
Witte
D T
DT
Grol
C J
CJ
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
D007202:Indicators and Reagents; D011956:Receptors, Cell Surface; D044094:Receptors, Melatonin; D002482:Cellulose; C024671:cellulose triacetate; D008550:Melatonin