Chiral recognition and the determination of optical purity of some amino acid ester salts using monosaccharides as chiral selectors under liquid secondary ion mass spectral conditions†

Abstract

Naturally occuring monosaccharides D-mannose, D-galactose and D-glucose have been used for the first time as co-matrices for chiral recognition and for the determination of optical purity of the enantiomers of α-amino acid methyl ester hydrochlorides.

References

1. M. Sawada, H. Yamaoka, Y. Takai, Y. Kawai, H. Yamada, T. Azuma, T. Fujioka and T. Tanaka, Chem. Commun., 1998, 1569.
2. Y.-N. Wu, Y.-P. Tu, Y.-J. Pan, Y.-Z. Chen, M. Cui, F.-R. Song and S.-Y. Liu, Anal. Lett., 1997, 30, 1399.
3. M. Sawada, Chiral mass spectrometry, in Biological Mass Spectrometry: Present and Future, ed. T. Matsu, R. M. Caprioli, M. L. Gross and Y. Sayama, Wiley, New York, 1994, p. 639.
4. M. Sawada, Y. Takai, H. Yamada, J. Nishida, T. Kaneda, R. Arakawa, M. Okamoto, K. Hirose, T. Tanaka and K. Naemura, J. Chem. Soc., Perkins Trans. 2, 1998, 701.
5. M. Sawada, Mass Spectrom. Rev., 1997, 16, 73.
6. M. Sawada, Y. Takai, H. Yamada, S. Hirayama, T. Kaneda, T. Tanaka, K. Kamada, T. Mizooku, S. Takeuchi, K. Ueno, K. Hirose, Y. Tobe and K. Naemura, J. Am. Chem. Soc., 1995, 117, 7726.
7. M. Sawada, Y. Takai, H. Yamada, T. Kaneda, K. Kamada, T. Mizooku, K. Hirose, Y. Tobe and K. Naemura, J. Chem. Soc., Chem. Commun., 1994, 2497.
8. M. Sawada, Y. Okumura, M. Shizuma, Y. Takai, Y. Hidaka, H. Yamada, T. Tanaka, T. Kaneda, K. Hirose, S. Misumi and S. Takahashi, J. Am. Chem. Soc., 1993, 115, 7381.
9. M. Sawada, Y. Okumura, H. Yamada, Y. Takai, S. Takahashi, T. Kaneda, K. Hirose and S. Misumi, Org. Mass Spectrom., 1993, 28, 1525.
10. M. Sawada, M. Shizuma, Y. Takai, H. Yamada, T. Kaneda and T. Hanafusa, J. Am. Chem. Soc., 1992, 114, 4405.
11. All the LSI mass spectra were recorded on an AutoSpec (Micromass, Manchester, UK) mass spectrometer using an OPUS V3.IX data system. The samples were ionized using a primary ion beam of caesium ions of 25 kV at the source temperature of 46 °C. The desorbed ions were accelerated to 8 kV. The spectra were obtained with a magnet scan rate of 3 s per decade over a mass range of m/z 1–400 under continuum mode. The IRIS values presented here are an average of 10 successive experiments and an averaged spectrum from each experiment is obtained via the accumulation of 15 consecutive scans..