Preparation and evaluation of new Pirkle type chiral stationary phases with long alkyl chains for the separation of amino acid enantiomers derivatized with NBD-F

(Note: The full text of this document is currently only available in the PDF Version )

Masaru Kato, Takeshi Fukushima, Tomofumi Santa, Kazuhiro Imai, Kenichiro Nakashima and Ryota Nishioka


Abstract

In order to improve the high-performance liquid chromatographic separation of α-amino acids derivatized with the fluorogenic reagent 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) on commercially available chiral stationary phases (CSPs) such as SUMICHIRAL OA-2500(S) (CSP 1) and OA-4700 (CSP 3), the preparation of two new CSPs (CSP 2 and CSP 4) having 11-aminoundecanoic acid between the aminopropyl silica gel support and the chiral moiety in CSP 1 and CSP 3 is described. CSP 2 and CSP 4 improved both the mutual and enantiomeric separation of NBD-amino acids compared with CSP 1 and CSP 3. Thus, 17 pairs of NBD-amino acid enantiomers and NBD-glycine were separated on CSP 2 except for six NBD-amino acids (D-Asn, D-Ser, D-Gln, L-Pro, L-Ser and Gly). CSP 2 and CSP 4 also showed better enantiomeric separation of NBD-amino acid esters and amides than CSP 1 and CSP 3. It was considered that the achiral long alkyl chains in the CSPs might form a hydrophobic space which assisted the stereoselective interaction of analytes with the chiral moiety by changing the environment around the chiral moiety. On CSP 1 and CSP 2, NBD-β-amino acid was also enantiomerically separated.


References

  1. R. Bhushan and S. Joshi, Biomed. Chromatogr., 1993, 7, 235 CAS.
  2. S. Görög and M. Gazdag, J. Chromatogr. B, 1994, 659, 51 CrossRef CAS.
  3. T. Toyo'oka, Biomed. Chromatogr., 1996, 10, 265 CrossRef CAS.
  4. K. Imai, T. Fukushima, T. Santa, H. Homma, K. Hamase, K. Sakai and M. Kato, Biomed. Chromatogr., 1996, 10, 303 CrossRef CAS.
  5. D. W. Asward, Anal. Biochem., 1984, 137, 405 CrossRef CAS.
  6. R. H. Buck and K. Krummen, J. Chromatogr., 1984, 315, 279 CrossRef CAS.
  7. N. Nimura and T. Kinoshita, J. Chromatogr., 1986, 352, 169 CrossRef CAS.
  8. R. H. Buck and K. Krummen, J. Chromatogr., 1987, 387, 255 CrossRef CAS.
  9. H. Brückner, R. Wittner and H. Godel, J. Chromatogr., 1989, 476, 73 CrossRef CAS.
  10. A. Jegorov, J. Tríska and T. Trnka, J. Chromatogr. A, 1994, 673, 286 CrossRef CAS.
  11. S. Einarsson, B. Josefsson, P. Möller and D. Sanchez, Anal. Chem., 1987, 59, 1191 CrossRef CAS.
  12. E. Okuma and H. Abe, J. Chromatogr. B, 1994, 660, 243 CrossRef CAS.
  13. P. Marfey, Carlsberg Res. Commun., 1984, 49, 591 Search PubMed.
  14. H. Brückner and C. Gah, J. Chromatogr., 1991, 555, 81 CrossRef.
  15. T. Toyo'oka and Y. M. Liu, Analyst, 1995, 120, 385 RSC.
  16. T. Toyo'oka, Y. M. Liu, N. Hanioka, H. Jinno, M. Ando and K. Imai, J. Chromatogr. A, 1994, 675, 79 CrossRef CAS.
  17. T. Toyo'oka, M. Ishibashi, T. Terao and K. Imai, Analyst, 1993, 118, 789 Search PubMed.
  18. K. Imai and Y. Watanabe, Anal. Chim. Acta, 1981, 130, 377 CrossRef CAS.
  19. N. Ôi, H. Kitahara, Y. Matsumoto, H. Nakajima and Y. Horikawa, J. Chromatogr., 1989, 462, 382 CrossRef CAS.
  20. N. Ôi, H. Kitahara, F. Aoki and N. Kisu, J. Chromatogr. A, 1995, 689, 195 CrossRef CAS.
  21. K. Imai, T. Fukushima and S. Uzu, Biomed. Chromatogr., 1993, 7, 177 CAS.
  22. K. Imai and T. Fukushima, Biomed. Chromatogr., 1993, 7, 275 CAS.
  23. T. Fukushima, M. Kato, T. Santa and K. Imai, Biomed. Chromatogr., 1995, 9, 10 CAS.
  24. K. Hamase, H. Homma, Y. Takigawa, T. Fukushima, T. Santa and K. Imai, Biochim. Biophys. Acta, 1997, 1334, 214 CrossRef CAS.
  25. K. Imai, T. Fukushima, K. Hagiwara and T. Santa, Biomed. Chromatogr., 1995, 9, 106 CAS.
  26. T. Fukushima, T. Santa, H. Homma, R. Nagatomo and K. Imai, Biol. Pharm. Bull., 1995, 18, 1130 Search PubMed.
  27. M. Kato, T. Fukushima, T. Santa, H. Homma and K. Imai, Biomed. Chromatogr., 1995, 9, 193 CAS.
  28. S. Akiyama, K. Nakashima, N. Shirakawa and K. Yamada, Bull. Chem. Soc. Jpn., 1990, 63, 2809 CAS.
  29. N. Bargmann-Leyder, J. C. Truffert, A. Tambuté and M. Caude, J. Chromatogr. A, 1994, 666, 27 CrossRef CAS.
  30. N. M. Maier and G. Uray, J. Chromatogr. A, 1996, 732, 215 CrossRef CAS.
  31. W. H. Pirkle and C. J. Welch, J. Liq. Chromatogr., 1992, 15, 1947 CAS.
  32. W. H. Pirkle and P. G. Murray, J. Chromatogr. A, 1996, 719, 299 CrossRef CAS.
  33. W. H. Pirkle and M. H. Hyun, J. Chromatogr., 1985, 328, 1 CrossRef CAS.
  34. Y. Dobashi and S. Hara, J. Org. Chem., 1987, 52, 2490 CrossRef CAS.
  35. W. H. Pirkle and C. J. Welch, J. Chromatogr., 1992, 589, 45 CrossRef CAS.
  36. J. A. W. Wildsmith, G. T. Tucker, S. Cooper, D. B. Scott and B. G. Covino, Br. J. Anaesth., 1977, 49, 461 Search PubMed.
  37. G. T. Tucker, L. E. Mather, M. S. Lennard and A. Gregory, Br. J. Anaesth., 1990, 65, 333 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.