title: Preparative HPLC resolution of the CIS cyclohexane analogs of phenylalanine.
abstract: The analytical resolution of different derivatives of cis c(6)Phe (cyclohexane analogs of phenylalanine) was tested by HPLC using the mixed 10-undecenoate/3,5-dimethylphenylcarbamate of amylose bonded on allylsilica gel as the chiral stationary phase. The same chiral support has allowed the enantioseparation of racemate cis-4 on a semipreparative column (150 x 20 mm ID) with a mixture of n-hexane/2-propanol/chloroform as the mobile phase. Some 200-300 mg of the optically pure enantiomers were isolated and transformed into the N-benzyloxycarbonyl amino acids. The X-ray diffraction structure of (1R;2R)-4 is reported.
authors.affiliation: Departamento de Química Orgánica, ICMA, Universidad de Zaragoza-CSIC, Zaragoza, Spain.
authors.forename: M
authors.initials: M
authors.lastname: Alías
authors.forename: C
authors.initials: C
authors.lastname: Cativiela
authors.forename: A I
authors.initials: AI
authors.lastname: Jiménez
authors.forename: P
authors.initials: P
authors.lastname: López
authors.forename: L
authors.initials: L
authors.lastname: Oliveros
authors.forename: M
authors.initials: M
authors.lastname: Marraud
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003510:Cyclohexanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D003510:Cyclohexanes; D010649:Phenylalanine