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Synthesis of dipeptide units of the D D configuration in aqueous media by enzymatic catalysis

Kempe, Maria LU ; Fischer, Lutz and Mosbach, Klaus LU (1993) In Journal of Molecular Recognition 6(1). p.25-29
Abstract
Novel molecularly imprinted polymer systems utilizing 4-vinylpyridine and 1-vinylimidazole as functional monomers have been developed for enantioselective recognition of carboxylic and N-protected amino acids. Non-covalent interactions between the functional monomers and the template molecules were the source of the subsequent recognition sites in the resultant polymers. The capacity of the polymers for molecular recognition was investigated by using them as stationary phases in the HPLC mode. Polymers prepared with 4-vinylpyridine were found to be more efficient in racemic resolution than those prepared with 1-vinylimidazole. When applying a racemic mixture of the template molecule, the polymers showed highest affinity for the enantiomer... (More)
Novel molecularly imprinted polymer systems utilizing 4-vinylpyridine and 1-vinylimidazole as functional monomers have been developed for enantioselective recognition of carboxylic and N-protected amino acids. Non-covalent interactions between the functional monomers and the template molecules were the source of the subsequent recognition sites in the resultant polymers. The capacity of the polymers for molecular recognition was investigated by using them as stationary phases in the HPLC mode. Polymers prepared with 4-vinylpyridine were found to be more efficient in racemic resolution than those prepared with 1-vinylimidazole. When applying a racemic mixture of the template molecule, the polymers showed highest affinity for the enantiomer used as template. Imprints of a racemic template molecule, as expected, did not exhibit enantioselectivity. The optimal molar ratio of 4-vinylpyridine to the template Cbz-L-Asp-OH in the polymerization mixture was determined to be 12:1. In addition to enantioselectivity, the investigated polymers demonstrated ligand selectivity e.g., a Cbz-L-Asp-OH-imprinted polymer was able to separate Cbz-D,L-Asp-OH, but was unable to separate Cbz-D,L-Glu-OH. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Molecular Recognition
volume
6
issue
1
pages
25 - 29
publisher
John Wiley & Sons
external identifiers
  • scopus:0027552762
ISSN
1099-1352
DOI
10.1002/jmr.300060103
language
English
LU publication?
yes
id
ba9ccc21-7bda-4a68-902c-e272e53ef4ca (old id 1516054)
date added to LUP
2009-12-17 08:40:00
date last changed
2017-11-05 03:37:03
@article{ba9ccc21-7bda-4a68-902c-e272e53ef4ca,
  abstract     = {Novel molecularly imprinted polymer systems utilizing 4-vinylpyridine and 1-vinylimidazole as functional monomers have been developed for enantioselective recognition of carboxylic and N-protected amino acids. Non-covalent interactions between the functional monomers and the template molecules were the source of the subsequent recognition sites in the resultant polymers. The capacity of the polymers for molecular recognition was investigated by using them as stationary phases in the HPLC mode. Polymers prepared with 4-vinylpyridine were found to be more efficient in racemic resolution than those prepared with 1-vinylimidazole. When applying a racemic mixture of the template molecule, the polymers showed highest affinity for the enantiomer used as template. Imprints of a racemic template molecule, as expected, did not exhibit enantioselectivity. The optimal molar ratio of 4-vinylpyridine to the template Cbz-L-Asp-OH in the polymerization mixture was determined to be 12:1. In addition to enantioselectivity, the investigated polymers demonstrated ligand selectivity e.g., a Cbz-L-Asp-OH-imprinted polymer was able to separate Cbz-D,L-Asp-OH, but was unable to separate Cbz-D,L-Glu-OH.},
  author       = {Kempe, Maria and Fischer, Lutz and Mosbach, Klaus},
  issn         = {1099-1352},
  language     = {eng},
  number       = {1},
  pages        = {25--29},
  publisher    = {John Wiley & Sons},
  series       = {Journal of Molecular Recognition},
  title        = {Synthesis of dipeptide units of the D D configuration in aqueous media by enzymatic catalysis},
  url          = {http://dx.doi.org/10.1002/jmr.300060103},
  volume       = {6},
  year         = {1993},
}