Preparative HPLC resolution of the CIS cyclohexane analogs of phenylalanine.
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.
Alías
M
M
Departamento de Química Orgánica, ICMA, Universidad de Zaragoza-CSIC, Zaragoza, Spain.
Cativiela
C
C
Jiménez
A I
AI
López
P
P
Oliveros
L
L
Marraud
M
M
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
D003510:Cyclohexanes; D010649:Phenylalanine