Document Detail


Chiral discrimination of β-3-homo-amino acids using the kinetic method.
MedLine Citation:
PMID:  20872892     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Chiral discrimination of seven enantiomeric pairs of β-3-homo-amino acids was studied by using the kinetic method and trimeric metal-bound complexes, with natural and unnatural α-amino acids as chiral reference compounds and divalent metal ions (Cu(2+) and Ni(2+) ) as the center ions. The β-3-homo-amino acids were selected for this study because, first of all, chiral discrimination of β-amino acids has not been extensively studied by mass spectrometry. Moreover, these β-3-homo-amino acids studied have different aromatic side chains. Thus, the emphasis was to study the effect of the side chain (electron density of the phenyl ring, as well as the difference between phenyl and benzyl side chains) for the chiral discrimination. The results showed that by the proper choice of a metal ion and a chiral reference compound, all seven enantiomeric pairs of β-3-homo-amino acids could be differentiated. Moreover, it was noted that the β-3-homo-amino acids with benzyl side chains provided higher enantioselectivity than the corresponding phenyl ones. However, increasing or decreasing the electron density of the aromatic ring by different substituents in both the phenyl and benzyl side chains had practically no role for chiral discrimination of β-3-homo-amino acids studied. When copper was used as the central metal, the phenyl side chain containing reference molecules (S)-2-amino-2-phenylacetic acid (L-Phg) and (S)-2-amino-2-(4-hydroxyphenyl)-acetic acid (L-4'-OHPhg) gave rise to an additional copper-reduced dimeric fragment ion, [Cu(I) (ref)(A)](+) . The inclusion of this ion improved noticeably the enantioselectivity values obtained.
Authors:
Róbert Berkecz; Anna R M Hyyryläinen; Ferenc Fülöp; Antal Péter; Tamás Janáky; Pirjo Vainiotalo; Jaana M H Pakarinen
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-09-25
Journal Detail:
Title:  Journal of mass spectrometry : JMS     Volume:  45     ISSN:  1096-9888     ISO Abbreviation:  J Mass Spectrom     Publication Date:  2010 Nov 
Date Detail:
Created Date:  2010-11-25     Completed Date:  2011-01-07     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9504818     Medline TA:  J Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  1312-9     Citation Subset:  IM    
Copyright Information:
Copyright © 2010 John Wiley & Sons, Ltd.
Affiliation:
Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry*
Kinetics
Spectrometry, Mass, Electrospray Ionization / methods*
Stereoisomerism
Tandem Mass Spectrometry / methods*
Chemical
Reg. No./Substance:
0/Amino Acids

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