A glycopeptide antibiotic chiral stationary phase for the enantiomer resolution of hydroxy acid derivatives by capillary electrochromatography.
Separation of hydroxy acid enantiomers was achieved by using capillary electrochromatography (CEC) employing a chiral stationary phase (CSP) based on MDL 63,246 (Hepta-Tyr), a macrocyclic antibiotic of the teicoplanin family. The chiral selector was chemically bonded to 5 num diol-modified silica particles and the CSP mixed with amino silica (3:1 w/w) was packed into a 75 num ID fused-silica capillary. The CEC experiments were carried out by using an aqueous reversed-phase mode for the enantiomeric resolution of hydroxy acid compounds. Good enantioresolution was achieved for mandelic acid (MA), m-hydroxymandelic acid (m-OH-MA), p-OH-MA, and 3-hydroxy-4-methoxymandelic acid (3-OH-4-MeO-MA). The CEC system was less enantioselective towards 2-phenyllactic acid (2-PhL) and 3-PhL while mandelic acid methyl ester (MA-Et-Est) enantiomers were not resolved. Several experimental parameters, such as organic solvent type and concentration, buffer pH, capillary temperature, on enantioresolution factor, retention time, and retention factor were studied.
Fanali
Salvatore
S
Istituto di Metodologie Chimiche, Consiglio Nazionale delle Ricerche, Area della Ricerca di Roma, Monterotondo Scalo (Roma), Italy. fanali@mlib.cnr.it
Catarcini
Paolo
P
Presutti
Carla
C
Quaglia
Maria G
MG
Righetti
Pier-Giorgio
PG
D000097:Acetonitriles; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002021:Buffers; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D006880:Hydroxy Acids / Q000032:analysis / Q000737:chemistry; D007773:Lactates / Q000032:analysis; D008333:Mandelic Acids / Q000032:analysis; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D017334:Teicoplanin / Q000031:analogs & derivatives / Q000737:chemistry; D013696:Temperature; D013995:Time
D000097:Acetonitriles; D000900:Anti-Bacterial Agents; D002021:Buffers; D006880:Hydroxy Acids; D007773:Lactates; D008333:Mandelic Acids; D012997:Solvents; C005434:atrolactic acid; D017334:Teicoplanin; C096602:MDL 63246