Revised structure of flavolipin and synthesis of its isomers

Tetrahedron Letters

Volumn 39, Issue 25, 1998, Pages 4497-4500

  Shiozaki, Masao ^a   Deguchi, Noriko ^a   Ishikawa, Tomio ^a   Haruyama, Hideyuki ^a   Kawai, Yohko ^b   Nishijima, Masahiro ^b  

^a DAIICHI SANKYO CO   (Japan)

^b NATIONAL INSTITUTE OF INFECTIOUS DISEASES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLAVOLIPIN; LIPID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHRYSEOBACTERIUM MENINGOSEPTICUM; ISOMER; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; SYNTHESIS;

CHRYSEOBACTERIUM MENINGOSEPTICUM; FLAVOBACTERIUM; NEGIBACTERIA;

EID: 0032543478     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00798-9     Document Type: Article

References (13)

1. 1. (a) Y. Kawai and I. Yano, Eur. J. Biochem., 136, 531-538 (1983).
2. (b) Y. Kawai, I. Yano, and K. Kaneda, Eur. J. Biochem., 171, 73-80 (1988).
3. (c) Y. Kawai, I. Yano, K. Kaneda, and E. Yabuuchi, Eur. J. Biochem., 175, 633-641 (1988).
4. 2. (a) Y. Kawai and K. Akagawa, Infection and Immunity, 57, 2086-2091 (1989).
5. (b) Y. Kawai, K. Kaneda, Y. Morisawa, and K. Akagawa, Infection and Immunity, 59, 2560-2566 (1991).
6. 3. D. H. Murray and J. Prokop, J. Pharm. Sci., 54, 1468-1473 (1965).
7. 4. M. Shiozaki, N. Deguchi, T. Mochizuki, and M. Nishijima, Tetrahedron Lett. 37, 3875-3876 (1996).
8. 5. Compound (7R) was already reported in the following articles: (a) I. Uchida, K. Yoshida, Y. Kawai, S. Takasa, Y. Itoh, H. Tanaka, M. Kohsaka, and H. Imanaka, J. Antibiotics, 38, 1476-1486 (1985), and
9. (b) I. Uchida, K. Yoshida, Y. Kawai, S. Takase, Y. Itoh, H. Tanaka, M. Kosaka, and H. Imanaka, Chem. Pharm. Bull., 33, 424-427 (1985).
10. 6. Compound (75) has been reported as belonging to the N-type calcium channel blockers from a marine bacterium, Cytophaga sp. SANK 71996. T. Morishita, A. Sato, M. Hisamoto, M. Oda, K. Matsuda, A. Ishii, and K. Kodama, J. Antibiotics, 50, 457-468 (1997).
11. 7. K. Yoshida, M. Iwami, Y. Umehara, M. Nishikawa, I. Uchida, M. Kohsaka, H. Aoki, and H. Imanaka, J. Antibiotics, 38, 1469-1475 (1985).
12. 3) δ 0.86 (12H, d, J=6.7 Hz), 1.12-1.20 (4H, m), 1.25 (34H, bs), 1.46-1.64 (6H, m), 2.30 (2H, t, J=7.5 Hz), 2.45-2.58 (2H, m), 3.88-4.12 (4H, m), 4.62 (1H, d, J=6.9 Hz), 5.18 (1H, quintet, 7=5.7-6.7 Hz), 5.3-5.8 (2H, broad, COOH, OH), 7.15 (1H, bs, NH), 7.62 (1H, d, J=6.9 Hz, NH).
13. 9. This compound was reported as WB-3559 D, isolated from Flavobacterium sp. No. 3559 (reference 7), and it was synthesized by Uchida et al (reference 5). Therefore, it becomes clear that flavolipin is the same compound as WB-3559 D.