Diastereochemical Differentiation of β-Amino Acids Using Host-Guest Complexes Studied by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry

Anna R M Hyyryläinen, Jaana M H Pakarinen, Pirjo Vainiotalo, G. Stájer, F. Fülöp

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1038-1045
Number of pages8
JournalJournal of the American Society for Mass Spectrometry
Volume18
Issue number6
DOIs
Publication statusPublished - Jun 2007

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Cyclotrons
Cyclotron resonance
Fourier Analysis
Mass spectrometry
Mass Spectrometry
Norbornanes
Fourier transforms
Ions
Amino Acids
Stereoselectivity
Molecules
Electrospray ionization
Electrospray Ionization Mass Spectrometry
Hydrogen Bonding
Density functional theory
Hydrogen bonds

ASJC Scopus subject areas

  • Structural Biology
  • Spectroscopy

Cite this

Diastereochemical Differentiation of β-Amino Acids Using Host-Guest Complexes Studied by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. / Hyyryläinen, Anna R M; Pakarinen, Jaana M H; Vainiotalo, Pirjo; Stájer, G.; Fülöp, F.

In: Journal of the American Society for Mass Spectrometry, Vol. 18, No. 6, 06.2007, p. 1038-1045.

Research output: Contribution to journalArticle

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