Polyproline derivatives as chiral selectors in high performance liquid chromatography: chromatographic and conformational studies.
A proline oligopeptide-derived chiral selector (CS), containing 3,5-dimethylphenylcarbamate residues on the 4 position of the pyrrolidine rings, was bonded to a silica gel chromatographic matrix by the N-terminal group. The chromatographic behaviour of the resulting chiral stationary phase (CSP) was compared with that of a CSP containing the analogous monomeric CS and that resulting from bonding of the polyproline-derived CS by the carboxy-terminal group using several solvents as mobile phase. The CSs were also studied from the conformational point of view in solution using circular dichroism and 13C NMR. A relationship was found between the presence of an ordered conformation in the particular conditions used and increased enantioselectivity.
Institute for Research in Biomedicine, Parc Científicas de Barcelona, Baldiri Reixac, 10-12, E-08028 Barcelona, Spain.
Raquel
R
Sancho
Cristina
C
Minguillón
D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods*; D002942:Circular Dichroism; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D048448:Phenylcarbamates / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives; D011487:Protein Conformation; D013237:Stereoisomerism
C504080:3,5-dimethylphenylcarbamate; D010455:Peptides; D048448:Phenylcarbamates; C011083:polyproline; D011392:Proline