Peculiarities of dansyl amino acid enantioselectivity using human serum albumin as a chiral selector.
This paper describes a novel approach to the study of enantioselectivity variations in a series of apolar D,l-dansyl amino acids with mobile phase pH and temperature on a human serum albumin (HSA) column. The obtained measurement selectivity data are investigated using a new chiral recognition model. This model is based on the formation of complexes between the solute molecule and the binding cavity of the HSA. The thermodynamic results are used to predict a difference in the enantioselectivity mechanism when the side-chain of an asymmetric carbon atom of dansyl amino acids (R group) is aliphatic or aromatic. It appears that the steric bulkiness and polarizability of this group are important parameters in the chiral recognition mechanism.
Peyrin
E
E
Laboratoire de Chimie Analytique, Faculté de Médecine et Pharmacie, Besancon, France.
Guillaume
Y C
YC
Guinchard
C
C
D000596:Amino Acids / Q000737:chemistry*; D003619:Dansyl Compounds / Q000737:chemistry*; D006801:Humans; D006863:Hydrogen-Ion Concentration; D012709:Serum Albumin / Q000737:chemistry*; D013237:Stereoisomerism; D013499:Surface Properties; D013696:Temperature; D013816:Thermodynamics
D000596:Amino Acids; D003619:Dansyl Compounds; D012709:Serum Albumin