JMSSJ On-line

JMSSJ On-line, Vol. 48 (2000) No. 2, pp. 141-144

Measurement of Chiral Recognition Properties of Crown Ethers Using Matrix Assisted Laser Desorption Ionization Mass Spectrometry		>> Full Text PDF >> References
*Masami SAWADA,^a) Manabu HARADA,^b) Yoshio TAKAI,^a) Kazurou NAKANO^c), Masao KURODA,^c) and Ryuichi ARAKAWA^b)** ^a) Materials Analysis Center, The Institute of Scientific and Industrial Research, Osaka University (8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan)* ^b) Department of Applied Chemistry, Kansai University (3-3-35 Yamate-cho, Suita, Osaka 564-0073, Japan) ^c) Center for Research and Education, Osaka University Medical School (2-2 Yamadaoka, Suita, Osaka 565-0871, Japan)

Hydrogen bonding host-guest complex ions between chiral crown ethers and chiral amino acid ester salts, detected by matrix assisted laser desorption ionization (MALDI) mass spectrometry (MS) with a DHBA or MSA matrix, were studied on the view point of chiral recognition properties of the chiral crown hosts. The chiral recognition property (I_R/I_S-dn value≅=1.0) obtained by the present MALDI-MS is sharply different from the I_R/I_S-dn value obtained by FAB-MS or ESI-MS (≠1.0) in the same host-guest combinations. The direct comparison on the basis of the I_R/I_S-dn values suggests that MALDI-MS is not a suitable measurement tool for chiral host-guest interactions probably because of the particular way of sample preparation involving a crystallization process.

Key words: MALDI mass spectrometry, Chiral recognition, Chiral crown ether, Amino acid ester, Deuterium labeling, Cyclofructan, Host-guest complex, Non-covalent chiral interactions

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