Separation of amino acid enantiomers by micelle-enhanced ultrafiltration

T.J.M. de Bruin, A.T.M. Marcelis, H. Zuilhof, L.M. Rodenburg, P.E.M. Overdevest, A. van der Padt, E.J.R. Sudhölter

Research output: Contribution to journalArticleAcademicpeer-review

38 Citations (Scopus)

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
Original languageEnglish
Pages (from-to)627-636
JournalChirality
Volume12
DOIs
Publication statusPublished - 2000

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Enantiomers
Ultrafiltration
Micelles
Amino acids
Amino Acids
Enantioselectivity
Glutamic Acid
Isoleucine
Chirality
Nonionic surfactants
Hydrophobicity
Anchors
Phenylalanine
Hydrophobic and Hydrophilic Interactions
Surface-Active Agents
Leucine
Copper
Ions
Derivatives
Substrates

Cite this

de Bruin, T. J. M., Marcelis, A. T. M., Zuilhof, H., Rodenburg, L. M., Overdevest, P. E. M., van der Padt, A., & Sudhölter, E. J. R. (2000). Separation of amino acid enantiomers by micelle-enhanced ultrafiltration. Chirality, 12, 627-636. https://doi.org/10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;2-1
de Bruin, T.J.M. ; Marcelis, A.T.M. ; Zuilhof, H. ; Rodenburg, L.M. ; Overdevest, P.E.M. ; van der Padt, A. ; Sudhölter, E.J.R. / Separation of amino acid enantiomers by micelle-enhanced ultrafiltration. In: Chirality. 2000 ; Vol. 12. pp. 627-636.
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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",
author = "{de Bruin}, T.J.M. and A.T.M. Marcelis and H. Zuilhof and L.M. Rodenburg and P.E.M. Overdevest and {van der Padt}, A. and E.J.R. Sudh{\"o}lter",
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de Bruin, TJM, Marcelis, ATM, Zuilhof, H, Rodenburg, LM, Overdevest, PEM, van der Padt, A & Sudhölter, EJR 2000, 'Separation of amino acid enantiomers by micelle-enhanced ultrafiltration', Chirality, vol. 12, pp. 627-636. https://doi.org/10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;2-1

Separation of amino acid enantiomers by micelle-enhanced ultrafiltration. / de Bruin, T.J.M.; Marcelis, A.T.M.; Zuilhof, H.; Rodenburg, L.M.; Overdevest, P.E.M.; van der Padt, A.; Sudhölter, E.J.R.

In: Chirality, Vol. 12, 2000, p. 627-636.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Separation of amino acid enantiomers by micelle-enhanced ultrafiltration

AU - de Bruin, T.J.M.

AU - Marcelis, A.T.M.

AU - Zuilhof, H.

AU - Rodenburg, L.M.

AU - Overdevest, P.E.M.

AU - van der Padt, A.

AU - Sudhölter, E.J.R.

PY - 2000

Y1 - 2000

N2 - 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

AB - 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

U2 - 10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;2-1

DO - 10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;2-1

M3 - Article

VL - 12

SP - 627

EP - 636

JO - Chirality

JF - Chirality

SN - 0899-0042

ER -