The two enantiomeric pairs of bicyclic isoxazoline acidic amino acids, designed as conformationally constrained homologues of glutamic acid, have been prepared by taking advantage of a nitrile oxide cycloaddition coupled to highly selective biocatalyzed transformations. All four isomeric target amino acids were obtained with enantiomeric excesses higher than 99%. The absolute configurations were attributed to the compounds under study by comparing the experimental and theoretical vibrational circular dichroism features of two selected reaction intermediates. These absolute configurations were further confirmed using experimental and theoretical specific rotations.

Enantiopure stereoisomeric homologues of glutamic acid: chemoenzymatic synthesis and assignment of their absolute configurations / G. Roda, P. Conti, M. De Amici, Jiangtao H., Prasad L. Polavarapu, C. De Micheli. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 15:19(2004 Oct 04), pp. 3079-3090. [10.1016/j.tetasy.2004.07.037]

Enantiopure stereoisomeric homologues of glutamic acid: chemoenzymatic synthesis and assignment of their absolute configurations

G. Roda
Primo
;
P. Conti
Secondo
;
M. De Amici;C. De Micheli
Ultimo
2004

Abstract

The two enantiomeric pairs of bicyclic isoxazoline acidic amino acids, designed as conformationally constrained homologues of glutamic acid, have been prepared by taking advantage of a nitrile oxide cycloaddition coupled to highly selective biocatalyzed transformations. All four isomeric target amino acids were obtained with enantiomeric excesses higher than 99%. The absolute configurations were attributed to the compounds under study by comparing the experimental and theoretical vibrational circular dichroism features of two selected reaction intermediates. These absolute configurations were further confirmed using experimental and theoretical specific rotations.
Bicyclic isoxazoline, alphaD theoretical estimation
Settore CHIM/08 - Chimica Farmaceutica
4-ott-2004
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/10767
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