title: Enantioselective high-performance liquid chromatographic separation of N-methyloxycarbonyl unsaturated amino acids on macrocyclic glycopeptide stationary phases.
abstract: This paper describes the enantiomeric resolution of a series of unsaturated N-methyloxycarbonyl-alpha-H-alpha-amino acids (N-MOC-alpha-amino acids) on macrocyclic glycopeptide stationary phases by means of high-performance liquid chromatography (HPLC). Three types of glycopeptide phases, i.e. Chirobiotic T, V and R, were evaluated in both reversed-phase (RP) and polar ionic mode (PIM). The best results in terms of enantioselectivity and resolution were obtained on Chirobiotic R phase, with the PIM mobile phase giving the highest resolution per min. Investigation of the pH of the reversed-phase mobile phase in the pH range 4.1-5.9 showed little effect on enantioselectivity. The method was applied for monitoring the conversion and product enantiomeric excess of an enzymatic hydrolysis reaction using N-MOC-alpha-H-alpha-amino acid esters as substrate.
authors.affiliation: DSM Pharma Chemicals, Department of Advanced Synthesis, Catalysis and Development, P.O. Box 18, 6160 MD Geleen, The Netherlands.
authors.forename: J M M
authors.initials: JM
authors.lastname: Boesten
authors.forename: M
authors.initials: M
authors.lastname: Berkheij
authors.forename: H E
authors.initials: HE
authors.lastname: Schoemaker
authors.forename: H
authors.initials: H
authors.lastname: Hiemstra
authors.forename: A L L
authors.initials: AL
authors.lastname: Duchateau
mesh_terms: D000596:Amino Acids / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D006020:Glycopeptides / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D006020:Glycopeptides