Biochemistry and molecular genetics of the biosynthesis of the earthy odorant methylisoborneol in Streptomyces coelicolor

Journal of the American Chemical Society

Volumn 130, Issue 28, 2008, Pages 8908-8909

  Wang, Chieh Mei ^a   Cane, David E ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYLALLYLTRANSFERASE; METHYLISOBORNEOL; METHYLTRANSFERASE; TERPENE DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CATALYSIS; MOLECULAR GENETICS; STREPTOMYCES COELICOLOR;

BORNANES; DNA, BACTERIAL; KINETICS; ODORS; POLYMERASE CHAIN REACTION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STREPTOMYCES COELICOLOR;

EID: 47349100497     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803639g     Document Type: Article

References (23)

1. Bentley, S. D.; et al., Nature 2002, 417, 141-147.
2. (a) Jiang, J.; He, X.; Cane, D. E. J. Am. Chem. Soc. 2006, 128, 8128-8129.
3. Jiang, J.; Cane, D. E. J. Am. Chem. Soc. 2008, 130, 428-429.
4. Jiang, J.; He, X.; Cane, D. E. Nat. Chem. Biol. 2007, 3, 711-715.
5. (b) Nawrath, T.; Dickschat, J. S.; Muller, R.; Jiang, J.; Cane, D. E.; Schulz, S. J. Am. Chem. Soc. 2008, 130, 430-431.
6. Dickschat, J. S.; Bode, H. B.; Mahmud, T.; Muller, R.; Schulz, S. J. Org. Chem. 2005, 70, 5174-5182.
7. Lin, X.; Hopson, R.; Cane, D. E. J. Am. Chem. Soc. 2006, 128, 6022-6023.
8. Zhao, B.; Lin, X.; Lei, L.; Lamb, D. C.; Kelly, S. L.; Waterman, M. R.; Cane, D. E. J. Biol. Chem. 2008, 283, 8183-8189.
9. Christianson, D. W. Chem. Rev. 2006, 106, 3412-3442.
10. Wise, M. L.; Savage, T. J.; Katahira, E.; Croteau, R. J. Biol. Chem. 1998, 273, 14891-14899.
11. Wise, M. L.; Croteau, R. In Comprehensive Natural Products Chemistry. Isoprenoids Including Carotenoids and Steroids; Cane, D. E., Ed.; Elsevier: Oxford, 1999; Vol. 2, p 97-153.
12. Lanza, E.; Palmer, J. K. Phytochemistry 1977, 16, 1555-1560.
13. Lanza, E.; Ko, K. H. J. Agric Food Chem. 1976, 24, 1247-1250.
14. (a) Schulz, S.; Dickschat, J. S. Nat. Prod. Rep. 2007, 24, 814-842.
15. (b) Gerber, N. N. Tetrahedron Lett. 1968, 2971-2974.
16. Buttery, R. G.; Garibaldi, J. A. J. Agric. Food Chem. 1976, 24, 1246-1247.
17. McCallum, R.; Pendleton, P.; Schumann, R.; Trinh, M. U. Analyst 1998, 123, 2155-2160.
18. Juttner, F.; Watson, S. B. Appl. Environ. Microbiol. 2007, 73, 4395-4406.
19. Bentley, R.; Meganathan, R. FEBS Lett. 1981, 125, 220-222.
20. See Supporting Information for a description of the synthesis and NMR spectroscopic characterization of (E)- and (Z)-2-methylgeraniol.
21. Dickschat, J. S.; Nawrath, T.; Thiel, V.; Kunze, B.; Muller, R.; Schulz, S. Angew. Chem., Int. Ed. 2007, 46, 8287-8290.
22. Croteau, R.; Shaskus, J.; Cane, D. E.; Saito, A.; Chang, C. J. Am. Chem. Soc. 1984, 106, 1142-1143.
23. Shortly after submission of the original version of this manuscript, Komatsu et al published the results of an independent study of methyl isoborneol synthesis which used bioinformatic analysis to identify the two candidate genes constituting the methylisoborneol synthase operon in seven Streptomyces species, including S. coelicolor, and the confirmation of this assignment by PCR amplification and heterologous expression in S. avermitilis of the operons from S. ambofaciens, S. lasaliensis, and Sac. erythraea. They also report the in vitro formation of methylisoborneol by incubation of GPP and SAM with recombinant S. lasaliensis methyl transferase and methylisoborneol synthase, as well as the conversion of GPP to 2-methylGPP by the S. lasaliensis methyl transferase. Komatsu, M.; Tsuda, M.; Omura, S.; Oikawa, H.; Ikeda, H. Proc Natl. Acad. Sci. U.S.A. 2008, 105, 7422-7427.