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Diastereochemical differentiation of beta-amino acids using host-guest complexes studied by Fourier transform ion
Anna R M Hyyryläinen1, Jaana M H Pakarinen, Pirjo Vainiotalo
1Department of Chemistry, University of Joensuu, 80101 Joensuu, Finland.
Abstract:
Host-guest complexes where tetraethyl resorcarene was the host molecule were used to study the stereoselectivity of diasteromeric pairs of di-endo- and di-exo-2,3-disubstituted norbornane and norbornene amino acids by ion-molecule reactions and collision-induced dissociation with electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI FT-ICR MS). Both methods showed stereoselectivity for the diastereomeric pairs. Particularly high selectivity was achieved for di-endo- and di-exo-2,3-disubstituted norbornane amino acids with ion-molecule reactions. Also, ab initio and hybrid density functional theory calculations were performed to study the different structures of the host-guest complexes. Hydrogen bonding was crucial for the calculated lowest energy structures, and sterical considerations satisfactorily explained the ion-molecule reaction results.
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