Studies on the biosynthesis of terpenoids produced by actinomycetes. Part 4. Formation of BE-40644 by the mevalonate and nonmevalonate pathways

Tetrahedron Letters

Volumn 39, Issue 51, 1998, Pages 9497-9500

  Seto, Haruo ^a   Orihara, Nobuyo ^a   Furihata, Kazuo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

BE 40644; Biosynthesis; Nonmevalonate pathway; Terpenoid

Indexed keywords

ACETIC ACID; BE 40644; CARBON 13; GLUCOSE; MENAQUINONE; MEVALONIC ACID; MK 9; TERPENOID; UNCLASSIFIED DRUG;

ACTINOBACTERIA; ARTICLE; BACTERIAL METABOLISM; BIOSYNTHESIS; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; FERMENTATION; ISOTOPE LABELING; NONHUMAN;

EID: 0032542140     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02154-6     Document Type: Article

References (20)

1. 1. For part 3, see N. Orihara, T. Kuzuyama, S. Takahashi, K. Furihata and H. Seto: J. Antibiot., 1998, 51, 676.
2. 2. K. Shin-ya, K. Furihata, Y. Hayakawa and H. Seto: Tetrahedron Lett., 1990, 31, 6025.
3. 3. S. Funayama, M. Ishibashi, K. Komiyama, S. Omura: J. Org. Chem., 1990, 55, 1132.
4. 4. K. Shiomi, H. Iinuma, H. Naganawa, K. Isshiki, T. Takeuchi and H. Umezawa: J. Antibiot., 1987, 40, 1740.
5. 5. K. Isshiki, T. Tamamura, T. Sawa, H. Naganawa, T. Takeuchi and H. Umezawa: J. Antibiot., 1986, 39, 1634.
6. 6. D. E. Cane, T. Rossi, A. M. Tillman and J. P. Pachlatko: J. Am. Chem. Soc., 1981, 103, 1838.
7. 7. M. Rohmer, M. Knani, P. Simonin, B. Sutter and H. Sahm: Biochem. J., 1993, 295, 517.
8. J. Schwender, M. Seemann, H. K. Lichtenthaler and M. Rohmer: Biochem. J., 1996, 316, 73.
9. 8. S. Takahashi, T. Kuzuyama, H. Watanabe and H. Seto: Proc. Natl. Acad. Sci. U. S. A., 1998, 95, 9879.
10. 9. T. Kuzuyama, S. Takahashi, H. Watanabe and H. Seto: Tetrahedron Lett., 1998, 39, 4509.
11. 10. T. Kuzuyama, T. Shimizu, S. Takahashi and H. Seto: Tetrahedron Lett., 1998, 39, 7913.
12. 11. N. Orihara, K. Furihata and H. Seto: J. Antibiot., 1997, 50, 979.
13. 12. S.-M. Li, S. Henning and L. Heide: Tetrahedron Lett., 1998, 39, 2717.
14. 13. H. Seto, H. Watanabe and K. Furihata: Tetrahedron Lett., 1996, 37, 7979.
15. 14. K Torigoe, N. Wakasugi, N. Sakaizumi, T. Ikejima, H. Suzuki, K. Kojiro and H. Suda: J. Antibiot, 1996, 49, 314.
16. 3 at 125 MHz.
17. 14 except for the exchange of C-14 and 15. The signal intensity of C-8 at 79.75 ppm was normalized to 1.0. 13.81 (C-13, 2.0), 16.70 (C-11, 1.2), 18.17 (C-6, 1.1), 18.32 (C-2, 1.1), 21.88 (C-14, 2.0), 27.20 (C-12, 2.0), 33.16 (C-4, 1.1), 33.66 (C-15, 2.0), 38.44 (C-10, 1.0), 39.65 (C-7, 2.1), 39.93 (C-1, 2.0), 41.63 (C-3, 1.8), 48.41 (C-9, 1.7), 55.07 (C-5, 1.8), 59.63 (C-22, 2.6), 79.75 (C-8, 1.0), 119.97 (C-16, 1.1), 131.66 (C-18, 1.8), 144.12 (C-19, 0.9), 153.62 (C-21, 1.2), 182.08 (C-20, 1.7), 186.67 (C-17, 0.9).
18. 13C]glucose at 58 hr showed a small contribution of the nonmevalonate pathway (data not shown).
19. 18. H. G. Floss: Nat. Prod. Reports, 1997, 14, 433.
20. 13. The signal intensity of C-3 of the unit 3 at 32.47 ppm was normalized to 1.0. 12.69 (3-Me; 1.1, 1.3), 16.03 (C-5 of unit 4∼8; 1.5, 2.0), 16.31 (C-5 of unit 1; 1.7, 2.3), 17.69 (C-5 of unit 9; 1.4, 2.2), 19.65 (C-5 of unit 2; 1.7, 2.0), 19.69 (C-5 of unit 3; 1.7, 2.0), 24.41 (C-1 of unit 3; 1.5, 1.3), 25.31 (C-1 of unit 2; 1.5, 1.5), 25.50 (C-1 of unit 4; 1.5, 1.3), 25.69 (C-4 of unit 9; 1.0, 1.7), 26.70 (X4) (C-1 of unit 5∼8; 1.4, 1.2), 26.78 (C-1 of unit 9; 1.4, 1.5), 32.47 (C-3 of unit 3; 1.0, 1.0), 32.65 (C-3 of unit 2; 1.0, 1.0), 36.68 (C-2 of unit 2; 1.1, 1.9), 37.13 (C-4 of unit 3; 1.1, 1.8), 37.29 (C-2 of unit 3; 1.1, 1.7), 37.40 (C-4 of unit 2; 1.2, 1.8), 39.73 (C-4 of units 4∼8; 1.1, 1.7), 40.04 (C-4 of unit 1; 1.2, 1.9), 118.81 (C-2 of unit 1; 1.0, 1.8), 124.28 (X4) (C-2 of units 5∼8; 0.9, 1.6), 124.41 (C-2 of unit 9; 1.1, 1.5), 124.96 (C-2 of unit 4; 1.0, 1.7), 126.19 and 126.31 (C-5 and C-8; 1.5, 1.0, and 2.1,1.0), 131.25 (C-3 of unit 9; 0.9, 1.1), 132.18 and 132.22 (C-9 and C-10; 1.2, 1.1 and 1.1, 1.1), 132.28 and 133.33 (C-6 and C-7; 1.5, 1.7 and 1.2, 1.7), 134.59 (C-3 of unit 4; 0.9, 1.0), 134.91 (X4) (C-3 of units 5∼8; 0.9, 1.0), 137.99 (C-3 of unit 1; 1.0, 1.1), 143.36 (C-3; 1.6, 2.2), 146.24 (C-2; 1.8, 1.8), 184.56 (C-1; 0.9, 1.0), 185.50 (C-4; 0.9, 1.0).