Chiral differentiation of some cyclopentane and cyclohexane beta-amino acid enantiomers through ion/molecule reactions.
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.
Hyyryläinen
Anna R M
AR
Department of Chemistry, University of Joensuu, Joensuu, Finland.
Pakarinen
Jaana M H
JM
Forró
Eniko
E
Fülöp
Ferenc
F
Vainiotalo
Pirjo
P
D000596:Amino Acids / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry; D003510:Cyclohexanes / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry
D000596:Amino Acids; D043844:Crown Ethers; D003510:Cyclohexanes; D003517:Cyclopentanes; D005021:Ethylamines; D047392:beta-Cyclodextrins; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid; C031215:betadex; C016162:triethylamine