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Issue 4, 2001
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Enantiospecific enzyme-catalysed resolution of novel N,N-disubstituted α-amino acid phenolic ester derivatives using pig liver esterase

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Abstract

R-Amino acid esters 1, 2 and 3 are novel compounds possessing hypnotic activity. On attempting an asymmetric synthesis of these molecules, racemisation was observed when reacting bis(2-methoxyethyl)amine with α-bromo intermediate 4. In vitro plasma stability studies showed that the R enantiomers had much greater resistance to esterase-mediated degradation than the corresponding S enantiomers. This observation led to the use of commercially available pig liver esterase to prepare 1, 2 and 3 on a multigram scale. The crystal structures of 1 and 2 are reported and confirm R configuration.

Graphical abstract: Enantiospecific enzyme-catalysed resolution of novel N,N-disubstituted α-amino acid phenolic ester derivatives using pig liver esterase

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Publication details

The article was received on 03 Oct 2000, accepted on 09 Jan 2001 and first published on 24 Jan 2001


Article type: Paper
DOI: 10.1039/B008000O
J. Chem. Soc., Perkin Trans. 1, 2001, 362-365

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    Enantiospecific enzyme-catalysed resolution of novel N,N-disubstituted α-amino acid phenolic ester derivatives using pig liver esterase

    D. J. Bennett, K. I. Buchanan, A. Cooke, O. Epemolu, N. M. Hamilton, E. J. Hutchinson and A. Mitchell, J. Chem. Soc., Perkin Trans. 1, 2001, 362
    DOI: 10.1039/B008000O

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