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Chiral recognition and separation of beta(2)-amino acids using noncovalently molecularly imprinted polymers

Shim, Y H; Yilmaz, Ecevit LU ; Solange, L A and Haupt, Karsten Olaf LU (2004) In Analyst 129(12). p.1211-1215
Abstract
Non-covalently molecularly imprinted polymers (MIPs) for beta(2)-amino acids were prepared for the first time. N-(2-chlorobenzyloxycarbonyl)-(R)-beta(2)-homophenylalanine (N-2-ClZ-(R)-beta(2)-HPhe)was imprinted with methacrylic acid (MAA) and/or 4-vinylpyridine (4-VPy) as the functional monomers, with ethylene glycol dimethacrylate ( EDMA) as the cross-linker. The MIPs made with different ratios of MAA:4-VPy were studied in HPLC mode. The results show that MIPs made with 4-VPy yielded the best chiral separation factor (alpha=1.86) for the template molecule. The importance for an efficient separation of pi-stacking interactions between the MIPs and the template molecule is demonstrated. Racemates of Z-alpha-amino acids and beta-amino acid... (More)
Non-covalently molecularly imprinted polymers (MIPs) for beta(2)-amino acids were prepared for the first time. N-(2-chlorobenzyloxycarbonyl)-(R)-beta(2)-homophenylalanine (N-2-ClZ-(R)-beta(2)-HPhe)was imprinted with methacrylic acid (MAA) and/or 4-vinylpyridine (4-VPy) as the functional monomers, with ethylene glycol dimethacrylate ( EDMA) as the cross-linker. The MIPs made with different ratios of MAA:4-VPy were studied in HPLC mode. The results show that MIPs made with 4-VPy yielded the best chiral separation factor (alpha=1.86) for the template molecule. The importance for an efficient separation of pi-stacking interactions between the MIPs and the template molecule is demonstrated. Racemates of Z-alpha-amino acids and beta-amino acid analogues of the template were either not or poorly resolved by the MIPs, thus demonstrating the close three-dimensional complementarity of the MIPs' recognition sites with the template. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Analyst
volume
129
issue
12
pages
1211 - 1215
publisher
Royal Society of Chemistry
external identifiers
  • pmid:15565220
  • wos:000225335500010
  • scopus:11944260598
ISSN
1364-5528
DOI
10.1039/b409836f
language
English
LU publication?
yes
id
f94d4f75-30d1-4aad-bb15-e34322a6fa49 (old id 140967)
date added to LUP
2007-07-17 08:08:57
date last changed
2017-01-01 07:02:30
@article{f94d4f75-30d1-4aad-bb15-e34322a6fa49,
  abstract     = {Non-covalently molecularly imprinted polymers (MIPs) for beta(2)-amino acids were prepared for the first time. N-(2-chlorobenzyloxycarbonyl)-(R)-beta(2)-homophenylalanine (N-2-ClZ-(R)-beta(2)-HPhe)was imprinted with methacrylic acid (MAA) and/or 4-vinylpyridine (4-VPy) as the functional monomers, with ethylene glycol dimethacrylate ( EDMA) as the cross-linker. The MIPs made with different ratios of MAA:4-VPy were studied in HPLC mode. The results show that MIPs made with 4-VPy yielded the best chiral separation factor (alpha=1.86) for the template molecule. The importance for an efficient separation of pi-stacking interactions between the MIPs and the template molecule is demonstrated. Racemates of Z-alpha-amino acids and beta-amino acid analogues of the template were either not or poorly resolved by the MIPs, thus demonstrating the close three-dimensional complementarity of the MIPs' recognition sites with the template.},
  author       = {Shim, Y H and Yilmaz, Ecevit and Solange, L A and Haupt, Karsten Olaf},
  issn         = {1364-5528},
  language     = {eng},
  number       = {12},
  pages        = {1211--1215},
  publisher    = {Royal Society of Chemistry},
  series       = {Analyst},
  title        = {Chiral recognition and separation of beta(2)-amino acids using noncovalently molecularly imprinted polymers},
  url          = {http://dx.doi.org/10.1039/b409836f},
  volume       = {129},
  year         = {2004},
}