Literature DB >> 19297192

Chiral differentiation of some cyclopentane and cyclohexane beta-amino acid enantiomers through ion/molecule reactions.

Anna R M Hyyryläinen1, Jaana M H Pakarinen, Eniko Forró, Ferenc Fülöp, Pirjo Vainiotalo.   

Abstract

Chiral differentiation of four enantiomeric pairs of beta-amino acids, cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclopentanecarboxylic acids (cyclopentane beta-amino acids), and cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclohexanecarboxylic acids (cyclohexane beta-amino acids) was performed successfully by using host-guest complexes and ion/molecule reactions. The experiments were conducted by using electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. The effect of a chiral host molecule was tested by using three different host compounds; (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid, (-)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid, and beta-cyclodextrin. This is the first time that small enantiomeric pairs with two chiral centers have been differentiated using ion/molecule reactions and host-guest complexes.

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Year:  2009        PMID: 19297192     DOI: 10.1016/j.jasms.2009.02.018

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN: 1044-0305            Impact factor:   3.109


  21 in total

Review 1.  The chemistry of 2-aminocycloalkanecarboxylic acids.

Authors:  F Fülöp
Journal:  Chem Rev       Date:  2001-07       Impact factor: 60.622

2.  The Stability of Cyclodextrin Complexes in Solution.

Authors:  Kenneth A. Connors
Journal:  Chem Rev       Date:  1997-08-05       Impact factor: 60.622

Review 3.  Molecular recognition and supramolecular chemistry in the gas phase.

Authors:  C A Schalley
Journal:  Mass Spectrom Rev       Date:  2001 Sep-Oct       Impact factor: 10.946

4.  Cavity effects on the enantioselectivity of chiral amido[4]resorcinarene stereoisomers.

Authors:  Bruno Botta; Deborah Subissati; Andrea Tafi; Giuliano Delle Monache; Antonello Filippi; Maurizio Speranza
Journal:  Angew Chem Int Ed Engl       Date:  2004-09-13       Impact factor: 15.336

5.  Stereoisomeric separation of pharmaceutical compounds using CE with a chiral crown ether.

Authors:  Lili Zhou; Zhihao Lin; Robert A Reamer; Bing Mao; Zhihong Ge
Journal:  Electrophoresis       Date:  2007-08       Impact factor: 3.535

6.  Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separations of chiral acids, bases, and amino acids by HPLC.

Authors:  Christian V Hoffmann; Reinhard Pell; Michael Lämmerhofer; Wolfgang Lindner
Journal:  Anal Chem       Date:  2008-10-15       Impact factor: 6.986

7.  Kinetic Resolution of d,l-Amino Acids Based on Gas-Phase Dissociation of Copper(II) Complexes.

Authors:  W A Tao; D Zhang; F Wang; P D Thomas; R G Cooks
Journal:  Anal Chem       Date:  1999-10-01       Impact factor: 6.986

8.  Diastereochemical differentiation of beta-amino acids using host-guest complexes studied by Fourier transform ion cyclotron resonance mass spectrometry.

Authors:  Anna R M Hyyryläinen; Jaana M H Pakarinen; Pirjo Vainiotalo; Géza Stájer; Ferenc Fülöp
Journal:  J Am Soc Mass Spectrom       Date:  2007-03-12       Impact factor: 3.109

9.  Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation.

Authors:  Xin Cong; Gregg Czerwieniec; Erica McJimpsey; Seonghee Ahn; Frederic A Troy; Carlito B Lebrilla
Journal:  J Am Soc Mass Spectrom       Date:  2006-02-14       Impact factor: 3.109

10.  Differentiation of diastereomeric cyclic beta-amino acids by varying the neutral reagent in ion/molecule reactions studied by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry.

Authors:  Anna R M Hyyryläinen; Jaana M H Pakarinen; Pirjo Vainiotalo; Ferenc Fülöp
Journal:  Rapid Commun Mass Spectrom       Date:  2008       Impact factor: 2.419

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  1 in total

1.  Hydrogen bonding in phosphonate cavitands: investigation of host-guest complexes with ammonium salts.

Authors:  Elina Kalenius; Raisa Neitola; Michele Suman; Enrico Dalcanale; Pirjo Vainiotalo
Journal:  J Am Soc Mass Spectrom       Date:  2009-12-11       Impact factor: 3.109

  1 in total

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