2026-03-06T09:06:11Z https://kansai-u.repo.nii.ac.jp/oai

oai:kansai-u.repo.nii.ac.jp:00011529 2023-05-15T18:29:15Z 528:1588:1595:1597

Chiral Recognition of 18-Crown-6-tetracarboxylic Acid toward Amino Acids and Organic Amines by Fast Atom Bombardment Mass Spectrometry.A Comparison with Capillary Electrophoresis Sawada, Masami Yamauchi, Yasuhiro Shizuma, Motohiro Takai, Yoshio Nakano, Kazurou Kuroda, Masao Arakawa, Ryuichi FAB mass spectrometry Capillary electrophoresis Chiral recognition Chiral crown ether Amino acid ester Deuterium labeling Host-guest complex Non-covalent chiral interactions Chiral recognition of the host-guest complexations between the (RRRR)-18-crown-6-tetracarboxylic acid (18 C6TCA) host (H) and α-amino acid or their ester derivative guests (G) has been systematically determined using both FAB mass spectrometry (MS) and capillary zone electrophoresis (CE). A comparison of these two techniques for the same series of guests was then done for the first lime. In the case of 18C6TCA，we found that there is no correlation between the chiral recognition obtained from FABMS (i.e.，the IRIS value)and from CE(i.e.，the α value in an aqueous buffer solution) covering three sets of guests including amino acids，amino acid esters，and primary aromatic amines. On the other hand. the former showed a good agreement with that from NMR (i.e.，the KR/Ks value: the ratio of the corresponding equilibrium constants)， supporting our earlier conclusion that FABMS is a good measurement tool for predicting differences (44G°values) in the respective chiral H-G interactions in solution. We also found that when a given guest changes from an amino acid to its corresponding amino acid　ester，the α value by CE dramatically changes from α>1.0 toα<1.0，though the IRIS value by FABMS does not show any such changes. These findings，were considered to be due to the characteristic contributions of the dissociable host's COOH functions under the experimental pH conditions in CE. Mass Spectrometry Society of Japan 2000 eng journal article VoR http://hdl.handle.net/10112/5991 https://kansai-u.repo.nii.ac.jp/records/11529 10.5702/massspec.48.380 AA1254271X 13408097 Journal of the Mass Spectrometry Society of Japan 48 6 380 386 https://kansai-u.repo.nii.ac.jp/record/11529/files/KU-1100-20000000-02.pdf application/pdf 610.1 kB 2019-05-23