Chiral Protonated Amino Acid Ester Discrimination by Acyclic Chiral Hosts Including D-Mannofuranose Moieties in Fast Atom Bombardment Mass Spectrometry Coupled with the Enantiomer Labeled Guest Method
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概要
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Chiral discrimination by novel chiral hosts 3 and 4, which consist of an oxyethylene chain and 2,3:5,6-di-O-cyclohexylidene-β-D-mannofuranose moieties at both ends, was examined considering several protonated amino acid isopropyl ester guests using fast atom bombardment mass spectrometry (FABMS) with the enantiomer deuterium-labeled guest method. Host 3 showed chiral discrimination toward several guests but with slightly smaller chiral discrimination abilities than host 2a, which consists of a bis-(oxyethylene) chain and 1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside moieties at both ends. Host 4 showed no enantioselectivity, possibly because chiral hosts do not show a pseudo-ring conformation having large open spaces in complexations with a chiral guest in regard to the steric effects of cyclohexylidene groups. In addition, to understand the chiral recognition mechanisms, the binding sites of hosts 3 and 4 were elucidated by ultraviolet-visible (UV-VIS) and proton nuclear magnetic resonance (1H-NMR) spectroscopy.
- 2009-10-01
著者
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NAKAMURA Masaki
Department of Psychiatry, Tohoku University Graduate School of Medicine
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Sato Hirofumi
Department of Surgery, Kanazawa University School of Medicine
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Shizuma Motohiro
Technochemistry Osaka Municipal Technical Research Institute
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Ono Daisuke
Department Of Civil Engineering The Graduate School Of Science And Technology Nihon University
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SHIZUMA Motohiro
Department of Biochemistry, Osaka Municipal Technical Research Institute
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TAKAI Yoshio
Materials Analysis Center, The Institute of Scientific and Industrial Research, Osaka University
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SUZUKI Takeyuki
Materials Analysis Center, The Institute of Scientific and Industrial Research, Osaka University
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Takeda Yuka
Department Of Applied Chemistry & Biochemistry Faculty Of Engineering Kumamoto University
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Takai Y
Materials Analysis Center The Institute Of Scientific And Industrial Research Osaka University
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Takai Y
The Institute Of Scientific And Industrial Research Osaka University
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Takai Yoshio
Materials Analysis Center The Institute Of Scientific And Industrial Research Osaka University
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Suzuki Takeyuki
Materials Analysis Center The Institute Of Scientific And Industrial Research Osaka University
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Shizuma Motohiro
Department Of Biochemistry Osaka Municipal Technical Research Institute
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Sato Hirofumi
Department Of Applied Chemistry Osaka University
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Nakamura Masaki
Department Of Biology Faculty Of Medicine Toho University
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Nakamura Masaki
Osaka Municipal Technical Res. Inst.
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Takai Y
Toyama Univ. Toyama
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Nakamura Masaki
Department Of Applied Physics Okayama University Of Science
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Ono Daisuke
Department Of Anesthesiology Okayama Red Cross Hospital
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Takai Yoshio
Material Analysis Center, The Institute of Scientific and Industrial Research, Osaka University
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Sato Hirofumi
Department of Biochemistry, Osaka Municipal Technical Research Institute
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