Synthesis of Four Lysine-Linked
Cereulide Analogues Showing Ionophoric Activity Towards Potassium
Cations as Lead Compounds for Emetic Toxin-Detection by Immunoassays

Arthit Makarasen; Toshio Nishikawa; Minoru Isobe

doi:10.1055/s-0029-1216837

PAPER

Synthesis of Four Lysine-Linked Cereulide Analogues Showing Ionophoric Activity Towards Potassium Cations as Lead Compounds for Emetic Toxin-Detection by Immunoassays

Arthit Makarasen^a, Toshio Nishikawa^a, Minoru Isobe*^a,b
^a Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan
^b Institute for Advanced Research, Nagoya University, Chikusa, Nagoya 464-8601, Japan
e-Mail: isobem@agr.nagoya-u.ac.jp; e-Mail: minoru@mx.nthu.edu.tw;

Abstract

Alle Artikel dieser Rubrik

Abstract

An improved total synthesis of the emetic toxin cereulide and the preparation of four lysine-linked cereulide analogues is described. The cereulide analogues are prepared by replacing one of the amino acid residues in cereulide with lysine. The cereulide analogues demonstrate ionophoric activity towards alkali metal ions and inorganic ammonium ions, and are currently being used to develop an enzyme-linked immunosorbent assay for cereulide.

Key words

cereulide - Bacillus cereus - peptide synthesis - ionophore - l-O-lysine

Volltext

Referenzen

References

1a Granum PE. Foodborne Pathogens 2005, 409

1b Schoeni JL. Lee Wong AC. J. Food Protect. 2005, 68: 636

1c Agata N. Ohta M. Yokoyama K. Int. J. Food Microbiol. 2002, 73: 23

1d Granum PE. Lund T. FEMS Microbiol. Lett. 1997, 157: 223

1e Agata N. Ohta M. Mori M. Curr. Microbiol. 1996, 33: 67

1f Hughes S. Bartholomew B. Hardy JC. Kramer JM. FEMS Microbiol. Lett. 1988, 52: 7

1g Melling J. Capel BJ. FEMS Microbiol. Lett. 1978, 4: 133

2a Agata N. Mori M. Ohta M. Suwan S. Ohtani I. Isobe M. FEMS Microbiol. Lett. 1994, 121: 31

2b Isobe M, and Ohta M. inventors; JP 07242643. ; Chem. Abstr. 1995, 124, 143741

3 Suwan S. Isobe M. Ohtani I. Agata N. Mori M. Ohta M. J. Chem. Soc., Perkin Trans. 1 1995, 765

4 Pitchayawasin S. Kuse M. Koga K. Isobe M. Agata N. Ohta M. Bioorg. Med. Chem. Lett. 2003, 13: 3507

5a Mahler H. Pasi A. Kramer JM. Schulte P. Scoging AC. Bär W. Krähenbühl S. N. Engl. J. Med. 1997, 336: 1142

5b Agata N. Ohta M. Mori M. Isobe M. FEMS Microbiol. Lett. 1995, 129: 17

5c Shinagawa K. Konuma H. Sekita H. Sugii S. FEMS Microbiol. Lett. 1995, 130: 87

6a Rajkovic A. Uyttendaele M. Ombregt S.-A. Jaaskelainen E. Salkinoja-Salonen M. Debevere J. J. Food Protect. 2006, 69: 847

6b Taylor JMW. Sutherland AD. Aidoo KE. Logan NA. FEMS Microbiol. Lett. 2005, 242: 313

6c Shinagawa K. Ueno Y. Hu D. Ueda S. Sugii S. J. Vet. Med. Sci. 1996, 58: 1027

7a Carlin F. Fricker M. Pielaat A. Heisterkamp S. Shaheen R. Salkinoja-Salonen M. Svensson B. Nguyen-The C. Ehling-Schulz M. Int. J. Food Microbiol. 2006, 109: 132

7b Shaheen R. Andersson MA. Apetroaie C. Schulz A. Ehling-Schulz M. Ollilainen V.-M. Salkinoja-Salonen MS. Int. J. Food Microbiol. 2006, 107: 287

7c Rajkovic A. Uyttendaele M. Debevere J. Commun. Agric. Appl. Biol. Sci. 2005, 70: 11

8a Rajkovic A. Uyttendaele M. Debevere J. Int. J. Food Microbiol. 2007, 114: 92

8b Andersson MA. Hakulinen P. Honkalampi-Haemaelaeinen U. Hoornstra D. Lhuguenot J.-C. Maeki-Paakkanen J. Savolainen M. Severin I. Stammati A.-L. Turco L. Weber A. Von Wright A. Zucco F. Salkinoja-Salonen M. Toxicon 2007, 49: 351

8c Akiba T. Chiba T. Arai T. Ikeuchi Y. Ibe A. Yanagawa Y. Kai A. Yano K. Morozumi S. Nihon Shokuhin Biseibutsu Gakkai Zasshi 2006, 23: 213

8d Rajkovic A. Uyttendaele M. Deley W. Van Soom A. Rijsselaere T. Debevere J. J. Microbiol. Meth. 2006, 65: 525

8e Lindback T. Granum PE. Methods Biotechnol. 2005, 21: 15

8f Kawamura-Sato K. Hirama Y. Agata N. Ito H. Torii K. Takeno A. Hasegawa T. Shimomura Y. Ohta M. Microbiol. Immunol. 2005, 49: 25

8g Kawamura K. Hirama Y. Agata N. Ito H. Nippon Rinsho Biseibutsugaku Zasshi 2004, 14: 146

8h Andersson MA. Jaaskelainen EL. Shaheen R. Pirhonen T. Wijinand LM. Salkinoja-Salonen MS. Int. J. Food Microbiol. 2004, 94: 175

8i Hoornstra D. Andersson MA. Mikkola R. Salkinoja-Salonen MS. Toxicol. In Vitro 2003, 17: 745

8j Jaaskelainen EL. Teplova V. Andersson MA. Andersson LC. Tammela P. Andersson MC. Pirhonen TI. Saris N.-EL. Vuorela P. Salkinoja-Salonen MS. Toxicol. In Vitro 2003, 17: 737

8k Jaaskelainen EL. Haggblom MM. Andersson MA. Vanne L. Salkinoja-Salonen MS. J. Food Protect. 2003, 66: 1047

9a Kawamura K. Hirama Y. Agata N. Ito H. Ohta M. Nippon Rinsho Biseibutsugaku Zasshi 2005, 15: 68

9b Haggblom MM. Apetroaie C. Andersson MA. Salkinoja-Salonen MS. Appl. Environ. Microbiol. 2002, 68: 2479

10a Pitchayawasin-Thapphasaraphong S. Isobe M. ITE Lett. Batteries, New Technol. Med. 2006, 7: 465

10b Pitchayawasin S. Isobe M. Kuse M. Franz T. Agata N. Ohta M. Int. J. Mass Spectrom. 2004, 235: 123

11a Chiba T. Akiba T. Ibe A. Arai T. Ikeuchi Y. Shibata M. Yanagawa Y. Yono K. Morozumi S. Nihon Shokuhin Biseibutsu Gakkai Zasshi 2006, 23: 137

11b Hormazabal V. Ostensvik O. O’Sullivan K. Granum PE. J. Liq. Chromatogr. Relat. Technol. 2004, 27: 2531

12a Fricker M. Messelhaeusser U. Busch U. Scherer S. Ehling-Schulz M. Appl. Environ. Microbiol. 2007, 73: 1892

12b Miyamoto T, and Uejo H. inventors; JP 20060006256. ; Chem. Abstr. 2006, 144, 101963

12c Sutherland A. inventors; GB 2407320. ; Chem. Abstr. 2005, 142, 429170

12d Ehling-Schulz M, and Scherer S. inventors; EP 1508622. ; Chem. Abstr. 2005, 142, 255725

12e Ehling-Schulz M, Fricker M, and Scherer S. inventors; EP 1500708. ; Chem. Abstr. 2005, 142, 171027

12f Miyamoto T. Kamikado H. Sasaki C. Sadakari K. Honjoh K.-I. Iio M. Biocontrol Sci. 2004, 9: 69

12g Nakano S. Maeshima H. Matsumura A. Ohno K. Ueda S. Kuwabara Y. Yamada T. J. Food Protect. 2004, 67: 1694

12h Ehling-Schulz M. Fricker M. Scherer S. FEMS Microbiol. Lett. 2004, 232: 189

13a Lequin RM. Clin. Chem. 2005, 51: 2415

13b Engvall E. Perlmann P. Immunochem. 1971, 8: 871

13c Van Weemen BK. Schuurs AHWM. FEBS Lett. 1971, 15: 232

14 Brinkley M. Bioconjugate Chem. 1992, 3: 2 and references cited therein

15a Isobe M. Ishikawa T. Suwan S. Agata N. Ohta M. Bioorg. Med. Chem. Lett. 1995, 5: 2855

15b Yokoyama K. Ito M. Agata N. Isobe M. Shibayama K. Horii T. Ohta M. FEMS Immunol. Med. Microbiol. 1999, 24: 115

16 Dhimitruka I. Santa Lucia JJ. Org. Lett. 2006, 8: 47 and references cited therein

17a Shiina I. Kubota M. Ibuka R. Tetrahedron Lett. 2002, 43: 7535

17b Shiina I. Ibuka R. Kobuta M. Chem. Lett. 2002, 286

18a Aketa K.-I. Terashima S. Yamada S.-I. Chem. Pharm. Bull. 1976, 24: 621

18b Koga K. Wu CC. Yamada S. Chem. Pharm. Bull. 1972, 20: 1272

19 Shin I. Lee M. Lee J. Jung M. Lee W. Yoon J. J. Org. Chem. 2000, 65: 7667

20 You S.-L. Kelly JW. J. Org. Chem. 2003, 68: 9506

21 Shinagawa K. Otake S. Matsusaka N. Sugii S. J. Vet. Med. Sci. 1992, 54: 443