Chiral recognition mechanism for the resolution of enantiomers on a highly effective HPLC chiral stationary phase derived from (R)-4-hydroxyphenylglycine
✍ Scribed by Myung Ho Hyun; Chung-Sik Min
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 191 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
A chiral stationary phase (CSP 1) prepared starting from (R)-4hydroxyphenylglycine and then grafting (R)-N-butanoyl-4-allyloxyphenylglycine Npropyl amide to silica gel was found to be very effective in separating the enantiomers of N-(3,5-dinitrobenzoyl)-␣-amino amides. From the chromatographic behaviors of the resolution of N-propyl amides, N,N-diethyl amides and ethyl esters of N-(3,5dinitrobenzoyl)-␣-amino acids and the resolution of various N-(substituted benzoyl)leucine N-propyl amides, the hydrogen bonding and thedonor-acceptor sites of the analyte for the interaction with the CSP have been proposed. Similarly, the hydrogen bonding donor and acceptor sites of the CSP for the interaction with the analyte have been proposed from the comparison of the chromatographic behaviors of the resolution of various N-(3,5-dinitrobenzoyl)-␣-amino N-propyl amides on modified CSPs (CSP 7 containing trifluoroacetyl group instead of the butanoyl group of CSP 1 and CSP 8 containing N,N-diethyl group instead of the N-propyl group of CSP 1) with those on CSP 1. By correlating the interaction sites of the CSP and their complementary interaction sites of the analyte, a chiral recognition mechanism which utilizes the two hydrogen bonding interactions and thedonor-acceptor interaction between (R)-CSP 1 and more retained analytes, (S)-N-(3,5-dinitrobenzoyl)-␣-amino amides, has been proposed.