A facile method for the preparation of α-methylene-γ-butyrolactones from tulip tissues by enzyme-mediated conversion

Tetrahedron Letters

Volumn 50, Issue 33, 2009, Pages 4751-4753

  Kato, Yasuo ^a   Yoshida, Hiroyuki ^a   Shoji, Kazuaki ^b   Sato, Yukio ^a   Nakajima, Noriyuki ^a   Ogita, Shinjiro ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b Toyama Agricultural Research Center   (Japan)

Author keywords

Methylene butyrolactone; Enzymatic transformation; Selective extraction; Tulip; Tulipalin; Tuliposide

Indexed keywords

6 TULIPOSIDE A; ALPHA METHYLENE BUTYROLACTONE; ENZYME; LACTONE DERIVATIVE; TULIPALIN B; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; ENZYME MECHANISM; ENZYME PURIFICATION; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INCUBATION TEMPERATURE; PH; ROOM TEMPERATURE; SYNTHESIS; TULIP;

TULIPA;

EID: 67649338449     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.018     Document Type: Article

References (30)

1. Tschesche R., Kaemmerer F.J., Wulff G., and Schoenbeck F. Tetrahedron Lett. 9 (1968) 701
2. Bergman B.H.H., and Beijersbergen J.C.M. Eur. J. Plant Path. 74 (1968) 157
3. Tschesche R., Kaemmerer F.J., and Wulff G. Chem. Ber. 102 (1969) 2057
4. Slob A., and Varekamp H.Q. Proc. Konik. Ned. Akad. West. Ser. C Biol. Med. Sci. 80 (1977) 201
5. Christensen L.P., and Kristiansen K. Contact Dermat. 40 (1999) 300
6. Shoji K., Ubukata M., Momonoi K., Tsuji T., and Morimatsu T. J. Jap. S. Hort. Sci. 74 (2005) 469
7. Slob A., Jekel B., de Jong B., and Schlatmann E. Phytochemistry 14 (1975) 1997
8. Kato, Y.; Shoji, K.; Ubukata, M.; Shigetomi, K.; Sato, Y.; Nakajima, N.; Ogita, S. Biosci. Biotechnol. Biochem., in press.
9. Hoffmann H.M.R., and Rabe J. Angew. Chem., Int. Ed. Engl. 24 (1985) 94
10. Jean M., Le Roch M., Renault J., and Uriac P. Org. Lett. 7 (2005) 2663
11. Kuroda M., Yoshida D., and Mizusaki S. Agric. Biol. Chem. 50 (1986) 243
12. Onuki, M.; Kinoshita, S. U.S. Patent 20080311478, 2008.
13. Trumbo D.L. Polymer. Bull. 35 (1995) 265
14. Daniel A. S.; Iinuma Y.; Arase S.; Nihei T. Japan Patent 2004271767, 2004.
15. Edward, P. J.; Qing, Y. U.S. Patent 20070122625, 2007.
16. Mosnáček J., and Matyjaszewski K. Macromolecules 41 (2008) 5509
17. Grieco P.A., and Hiroi K. J. Chem. Soc. Chem. Commun. (1972) 1317
18. Griffin G.W., Nishiyama K., and Ishikawa K. J. Org. Chem. 42 (1977) 180
19. Murray T.F., Samsel E.G., Varma V., and Norton J.R. J. Am. Chem. Soc. 103 (1981) 7520
20. Brzezinski L.J., Rafel S., and Leahy W. Tetrahedron 53 (1997) 16423
21. Schlewer G., Stampf J.-L., and Benezra C. J. Med. Chem. 23 (1980) 1031
22. Hoffmann H.M.R., and Rabe J. Angew. Chem., Int. Ed. Engl. 24 (1985) 94
23. Barbier P., and Benezra C. J. Med. Chem. 29 (1986) 868
24. Dinprasert P., Mahidol C., Thebtaranonth C., and Thebtaranonth Y. Tetrahedron Lett. 30 (1989) 1149
25. Ohgiya T., and Nishiyama S. Hetrocycles 63 (2004) 2349
26. 4 in 10% MeOH.
27. 8
28. After enzymatic conversion, NaCl was added to the mixture until saturation, 2a was extracted with solvent-1 (200 μL × 2, 100 μL × 1), and the 2b remaining in the mixture was extracted with solvent-2 (200 μL × 2, 100 μL × 1). Both the extracts were combined and analyzed by gas chromatography (DB-5 column; Agilent technologies).
29. 16
30. 16