Resolution and conformational analysis of diastereoisomeric esters of cis- and trans-2-(aminomethyl)-1-carboxycyclopropanes |
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| Institution: | 1. Institut de Pharmacologie de Sherbrooke, Département de Pharmacologie-Physiologie, Faculté de Médecine et des Sciences de la santé, Université de Sherbrooke, Sherbrooke, QC, Canada;2. Institut de Pharmacologie de Sherbrooke, Département de Biochimie Et Génomique Fonctionnelle, Faculté de Médecine et des Sciences de la Santé, Université de Sherbrooke, Sherbrooke, QC, Canada;1. Biological and Chemical Research Center, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury Street 101, Warsaw 02-089, Poland;2. Department of Materials Science and Technology, University of Crete, Crete, Heraklion 70013, Greece;3. Foundation for Research and Technology – Hellas, Institute of Electronic Structure and Laser, Crete, Heraklion 70013, Greece |
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| Abstract: | (1R,2S)-, (1S,2R)-, (1R,2R)- and (1S,2S)-2-(Aminomethyl)-1-carboxycyclopropanes, conformationally restricted analogues of the neurotransmitter γ-aminobutyric acid (GABA), have been resolved by chromatographic separation of the corresponding diastereoisomeric esters which were formed between the cis- and trans-2-(acetamidomethyl)-1-carboxycyclopropanes with (R)-(−)-pantolactone. 1H NMR, semi-empirical conformational analysis, ab initio (DFT) structure and NMR shielding tensor calculations of the cis-diastereoisomers allowed the absolute configuration assignments of the cis-amino acids. |
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