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 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.
Hyyryläinen
Anna R M
AR
Department of Chemistry, University of Joensuu, 80101 Joensuu, Finland.
Pakarinen
Jaana M H
JM
Vainiotalo
Pirjo
P
Stájer
Géza
G
Fülöp
Ferenc
F
D000596:Amino Acids / Q000737:chemistry*; D017357:Cyclotrons; D012680:Sensitivity and Specificity; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods*; D013237:Stereoisomerism
D000596:Amino Acids