Dynamic ligand-exchange chiral stationary phase from S-benzyl-(R)-cysteine

S‐Benzyl‐(R)‐cysteine (R‐SBC) is a new chiral ligand‐exchange stationary phase which has proved to be effective in the analytical separation of some natural and unnatural underivatized amino acids with fair to good separation and resolution factors. The dynamic coating of the RP‐18 solid support wit...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2006, Vol.18 (7), p.509-518
Main Authors: Natalini, B., Sardella, R., Macchiarulo, A., Pellicciari, R.
Format: Article
Language:English
Subjects:
Amino Acids - analysis
Amino Acids - chemistry
chiral coated phase
Chromatography, Liquid - instrumentation
Chromatography, Liquid - methods
Cysteine - analysis
Cysteine - chemistry
enantiomer separation
Hydrogen-Ion Concentration
hydrophobically coated phase
Ligands
mechanism of recognition
Models, Molecular
Molecular Structure
Stereoisomerism
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Summary:S‐Benzyl‐(R)‐cysteine (R‐SBC) is a new chiral ligand‐exchange stationary phase which has proved to be effective in the analytical separation of some natural and unnatural underivatized amino acids with fair to good separation and resolution factors. The dynamic coating of the RP‐18 solid support with S‐Benzyl‐(R)‐cysteine (R‐SBC) gives rise to a stable and efficient chiral stationary phase (CSP) that has been successfully employed. The mechanism of chiral recognition is discussed and a molecular modeling study aimed at identifying molecular descriptors responsible for observed different behaviours of analytes upon different albeit closely related selectors is discussed. Chirality 18:509–518, 2006. © 2006 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.20280