Diastereochemical differentiation of [beta]-amino acids using host-guest complexes studied by fourier transform ion cyclotron resonance mass spectrometry

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 ioniza...

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Bibliographic Details
Published in:Journal of the American Society for Mass Spectrometry 2007-06, Vol.18 (6), p.1038
Main Authors: Hyyryläinen, Anna R, M, Pakarinen, Jaana M, H, Vainiotalo, Pirjo, Stájer, Géza, Fülöp, Ferenc
Format: Article
Language:English
Subjects:
Amino acids
Chemical bonds
Cyclotron resonance
Fourier transforms
Hydrogen bonding
Ionization
Ions
Mass spectrometry
Mathematical analysis
Scientific imaging
Selectivity
Spectroscopy
Stereoselectivity
Supramolecular compounds
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Summary: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.
ISSN:1044-0305
1879-1123
DOI:10.1016/j.jasms.2007.03.002