Chiral Recognition of N-Phthaloyl, N-Tetrachlorophthaloyl, and N-Naphthaloyl alpha-Amino Acids and Their Esters on Polysaccharide-Derived Chiral Stationary Phases
- Authors
- Kim, Byoung-Hyoun; Lee, Sang Uck; Moon, Dong Cheul
- Issue Date
- Dec-2012
- Publisher
- John Wiley & Sons Inc.
- Keywords
- chiral recognition; alpha-amino acid; HPLC; enantioseparation; polysaccharide-derived chiral stationary phase
- Citation
- Chirality, v.24, no.12, pp 1037 - 1046
- Pages
- 10
- Indexed
- SCI
SCIE
SCOPUS
- Journal Title
- Chirality
- Volume
- 24
- Number
- 12
- Start Page
- 1037
- End Page
- 1046
- URI
- https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/31327
- DOI
- 10.1002/chir.22094
- ISSN
- 0899-0042
1520-636X
- Abstract
- Enantiomeric separations of N-phthaloyl (N-PHT), N-tetrachlorophthaloyl (N-TCPHT), and N-naphthaloyl (N-NPHT) alpha-amino acids and their esters were examined on several kinds of polysaccharide-derived chiral stationary phases (CSPs). Resolution capability of CSPs was greater Chiralcel OF than the others for N-PHT and N-NPHT alpha-amino acids and their esters. In N-TCPHT alpha-amino acids and their esters, good enantioselectivities showed Chiralcel OG for N-TCPHT alpha-amino acids, Chiralpak AD for N-TCPHT alpha-amino acid methyl esters, and Chiralcel OD for N-TCPHT alpha-amino acid ethyl esters, respectively. From the results of liquid chromatography and computational chemistry, it is concluded that l-form is preferred and more retained with electrostatic interaction in case of interaction between N-PHT alpha-amino acid derivatives and Chiralcel OF, N-TCPHT alpha-amino acid derivatives and Chiralcel OD, and N-NPHT alpha-amino acid derivatives and Chiracel OF. On the other hand, d-form is preferred and more retained with van der Waals interaction in case of interaction between N-TCPHT alpha-amino acid ester derivatives and Chiralcel OG and Chiralpak AD. Chirality 24:10371046, 2012. (c) 2012 Wiley Periodicals, Inc.
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Collections - COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY > DEPARTMENT OF CHEMICAL AND MOLECULAR ENGINEERING > 1. Journal Articles
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