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Molecularly Imprinted Polymeric Adsorbents for Byproduct Removal

Ye, Lei LU orcid ; Ramström, Olof and Mosbach, Klaus LU (1998) In Analytical Chemistry 70(14). p.2789-2795
Abstract

In this study, both diastereo- and enantioselective adsorbents for a dipeptide derivative were prepared using a molecular imprinting technique. The diastereo- and enantioisomers for the dipeptide derivative N-(benzyloxy-carbonyl)aspartylphenylalanine methyl ester (ZAPM), in addition to the α- and β-isomers, were chosen as test compounds for the investigation of the imprinting effect The close similarities between the structures of different isomers make it possible to interpret the roles of template structure on specific molecular recognition. A highly specific byproduct scavenger was prepared by simultaneously incorporating methacrylic acid and vinylpyridine as functional monomers. The binding selectivities of polymeric adsorbents for... (More)

In this study, both diastereo- and enantioselective adsorbents for a dipeptide derivative were prepared using a molecular imprinting technique. The diastereo- and enantioisomers for the dipeptide derivative N-(benzyloxy-carbonyl)aspartylphenylalanine methyl ester (ZAPM), in addition to the α- and β-isomers, were chosen as test compounds for the investigation of the imprinting effect The close similarities between the structures of different isomers make it possible to interpret the roles of template structure on specific molecular recognition. A highly specific byproduct scavenger was prepared by simultaneously incorporating methacrylic acid and vinylpyridine as functional monomers. The binding selectivities of polymeric adsorbents for the α- and β-isomers are shown to be greatly enhanced by introducing enantiocomplementarities into the polymer matrixes. An anti-β-L,L-ZAPM polymer was applied in a solid-phase extraction protocol, for the purification of the product in the chemical synthesis of N-protected aspartame. Finally, polymer beads were also imprinted against β-L,L-ZAPM using suspension polymerization performed in perfluorocarbon fluid. The imprinted polymer beads displayed the same binding characteristics as the imprinted bulk polymer and can be envisaged for the use of product purification in chromatographic mode.

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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Analytical Chemistry
volume
70
issue
14
pages
7 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:0001712009
ISSN
0003-2700
DOI
10.1021/ac980069d
language
English
LU publication?
yes
id
56638ad1-bee0-4b2d-aa24-5cec810099ac
date added to LUP
2019-06-18 09:06:32
date last changed
2022-01-31 21:57:33
@article{56638ad1-bee0-4b2d-aa24-5cec810099ac,
  abstract     = {{<p>In this study, both diastereo- and enantioselective adsorbents for a dipeptide derivative were prepared using a molecular imprinting technique. The diastereo- and enantioisomers for the dipeptide derivative N-(benzyloxy-carbonyl)aspartylphenylalanine methyl ester (ZAPM), in addition to the α- and β-isomers, were chosen as test compounds for the investigation of the imprinting effect The close similarities between the structures of different isomers make it possible to interpret the roles of template structure on specific molecular recognition. A highly specific byproduct scavenger was prepared by simultaneously incorporating methacrylic acid and vinylpyridine as functional monomers. The binding selectivities of polymeric adsorbents for the α- and β-isomers are shown to be greatly enhanced by introducing enantiocomplementarities into the polymer matrixes. An anti-β-L,L-ZAPM polymer was applied in a solid-phase extraction protocol, for the purification of the product in the chemical synthesis of N-protected aspartame. Finally, polymer beads were also imprinted against β-L,L-ZAPM using suspension polymerization performed in perfluorocarbon fluid. The imprinted polymer beads displayed the same binding characteristics as the imprinted bulk polymer and can be envisaged for the use of product purification in chromatographic mode.</p>}},
  author       = {{Ye, Lei and Ramström, Olof and Mosbach, Klaus}},
  issn         = {{0003-2700}},
  language     = {{eng}},
  month        = {{07}},
  number       = {{14}},
  pages        = {{2789--2795}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Analytical Chemistry}},
  title        = {{Molecularly Imprinted Polymeric Adsorbents for Byproduct Removal}},
  url          = {{http://dx.doi.org/10.1021/ac980069d}},
  doi          = {{10.1021/ac980069d}},
  volume       = {{70}},
  year         = {{1998}},
}