Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 66336
Title Separation of amino acid enantiomers by micelle-enhanced ultrafiltration
Author(s) Bruin, T.J.M. de; Marcelis, A.T.M.; Zuilhof, H.; Rodenburg, L.M.; Overdevest, P.E.M.; Padt, A. van der; Sudhölter, E.J.R.
Source Chirality 12 (2000). - ISSN 0899-0042 - p. 627 - 636.
DOI https://doi.org/10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;2-1
Department(s) Organic Chemistry
Sub-department of Food and Bioprocess Engineering
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2000
Abstract A Micelle-enhanced ultrafiltration (MEUF) separation process was investigated that can potentially be used for large-scale enantioseparations. Copper(II)-amino acid derivatives dissolved in nonionic surfactant micelles were used as chiral selectors for the separation of dilute racemic amino acids solutions. For the α-amino acids phenylalanine, phenylglycine, O- methyltyrosine, isoleucine, and leucine good separation was obtained using cholesteryl L-glutamate and Cu(II) ions as chiral selector with an operational enantioselectivity (α(op)) up to 14.5 for phenylglycine. From a wide set of substrates, including four β-amino acids, it was concluded that the performance of this system is determined by two factors: the hydrophobicity of the racemic amino acid, which results in a partitioning of the racemic amino acid over micelle and aqueous solution, and the stability of the diastereomeric complex formed upon binding of the amino acid with the chiral selector. The chiral hydrophobic cholesteryl anchor of the chiral selector also plays an active role in the recognition process, since inversion of the chirality of the glutamate does not yield the reciprocal enantioselectivities. However, if the cholesteryl group is replaced by a nonchiral alkyl chain, reciprocal operational enantioselectivities are found with enantiomeric glutamate selectors
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