Diastereochemical differentiation of beta-amino acids using host-guest complexes studied by Fourier transform ion cyclotron resonance mass spectrometry.
J Am Soc Mass Spectrom
; 18(6): 1038-45, 2007 Jun.
Article
en En
| MEDLINE
| ID: mdl-17434744
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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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Ciclotrones
/
Espectroscopía Infrarroja por Transformada de Fourier
/
Espectrometría de Masa por Ionización de Electrospray
/
Aminoácidos
Tipo de estudio:
Diagnostic_studies
Idioma:
En
Revista:
J Am Soc Mass Spectrom
Año:
2007
Tipo del documento:
Article
País de afiliación:
Finlandia