Biosynthesis of polyunsaturated short chain aldehydes in the diatom Thalassiosira rotula

Organic Letters

Volumn 9, Issue 6, 2007, Pages 1017-1020

  Barofsky, Alexandra ^a   Pohnert, Georg ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2E,4Z,7Z DECATRIENAL; 2E,4Z,7Z-DECATRIENAL; ALDEHYDE; ALKENE; CYTOCHROME P450; ESTER; HYDROPEROXIDE LYASE; LIPOXYGENASE; LYASE; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ARTICLE; BIOLOGY; CHEMICAL MODEL; CHEMISTRY; DIATOM; METABOLISM;

ALDEHYDE-LYASES; ALDEHYDES; ALKENES; CYTOCHROME P-450 ENZYME SYSTEM; DIATOMS; ESTERS; FATTY ACIDS, UNSATURATED; LIPOXYGENASE; MARINE BIOLOGY; MODELS, CHEMICAL;

EID: 33947599707     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063051v     Document Type: Article

References (24)

1. Miralto, A.; Barone, G.; Poulet, S. A.; Ianora, A.; Russo, G. L.; Buttino, I.; Mazzarella, G.; Laabir, M.; Cabrini, M.; Giacobbe, M. G. Nature 1999, 402, 173.
2. Ianora, A.; Miralto, A.; Poulet, S. A.; Carotenuto, Y.; Buttino, I.; Romano, G.; Casotti, R.; Pohnert, G.; Wichard, T.; Colucci-D'Amato, L.; Terrazzano, G.; Smetacek, V. Nature 2004, 429, 403.
3. Pohnert, G. Angew. Chem., Int. Ed. 2000, 39, 4352.
4. Pohnert, G. ChemBioChem 2005, 6, 946.
5. Wichard, T.; Poulet, S. A.; Halsband-Lenk, C.; Albaina, A.; Harris, R.; Liu, D. Y.; Pohnert, G. J. Chem. Ecol. 2005, 31, 949.
6. d'Ippolito, G.; Tucci, S.; Cutignano, A.; Romano, G.; Cimino, G.; Miralto, A.; Fontana, A. Biochim. Biophys. Acta 2004, 1686, 100.
7. Pohnert, G. Plant Phys. 2002, 129, 103.
8. d'Ippolito, G.; Romano, G.; Caruso, T.; Spinella, A.; Cimino, G.; Fontana, A. Org. Lett. 2003, 5, 885.
9. Pohnert, G.; Adolph, S.; Wichard, T. Chem. Phys. Lipids 2004, 131, 159.
10. d'Ippolito, G.; Cutignano, A.; Tucci, S.; Romano, G.; Cimino, G.; Fontana, A. Phytochemistry 2006, 67, 314.
11. Noordermeer, M. A.; Veldink, G. A.; Vliegenthart, J. F. ChemBioChem 2001, 2, 494.
12. Gerwick, W. H. Biochim. Biophys. Acta 1994, 1211, 243.
13. Wichard, T.; Pohnert, G. J. Am. Chem. Soc. 2006, 128, 7114.
14. Synthesis of 9: Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4743.
15. Synthesis of 8: Funk, R. L.; Abelman, M. M.; Munger, J. D. Tetrahedron 1986, 42, 2831.
16. Synthesis of 8-hydroxy-6E-octenoic acid: Abelman, M. M.; Funk, R. L.; Munger, J. D., Jr. J. Am. Chem. Soc. 1982, 104, 4030.
17. Synthesis of 4: Falck, J. R.; Barma, D. K.; Mohapatra, S.; Bandyopadhyay, A.; Reddy, K. M.; Qi, J. J.; Campbell, W. B. Bioorg. Med. Chem. Lett. 2004, 14, 4987.
18. 18 column (2.1 mm, 1.7 μm), 4 min 0-50% B, 5 min 100% B, 5.5 min 0% B with a flow rate of 0.6 mL/min.
19. Compound 9: m/z calcd for M - H 157.0865, detected 157.0884. Compound 8: m/z calcd for M - H 157.0865, detected 157.0884. Compound 4: m/z calcd for M - H 183.1021, detected 183.1031.
20. Vick, B. A.; Zimmerman, D. C. Plant Phys. 1989, 90, 125.
21. Grechkin, A. N.; Hamberg, M. Biochim. Biophys. Acta 2004, 1636, 47.
22. Hombeck, M.; Pohnert, G., Boland, W. Chem. Commun. 1999, 243.
23. Wichard, T.; Göbel, C.; Feussner, I.; Pohnert, G. Angew. Chem., Int. Ed 2005, 44, 158.
24. Senger, T.; Wichard, T.; Kunze, S.; Göbel, C.; Lerchl, J.; Pohnert, G.; Feussner, I. J. Biol. Chem. 2005, 280, 7588.