Structure of blasticidin A

Tetrahedron Letters

Volumn 38, Issue 42, 1997, Pages 7399-7402

  Sakuda, Shohei ^a   Makoto, Ono ^b   Ikeda, Hiroyuki ^a   Inagaki, Yasuhito ^a   Nakayama, Jiro ^a   Suzuki, Akinori ^a   Isogai, Akira ^c  

^a UNIVERSITY OF TOKYO   (Japan)

^b Morinaga and Company Limited   (Japan)

^c NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BLASTICIDIN A; TETRAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0343247727     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01734-6     Document Type: Article

References (10)

1. Fukunaga, K.; Misato, T.; Ishii, L; Asakawa, M. Bull. Agr. Chem. Soc. Jap., 1955, 19, 181-188.
2. Kono, Y.; Takeuchi, S.; Yonehara, H. J. Antibiot., 1968, 21, 433-438.
3. Ono, M.; Sakuda, S.; Suzuki, A.; Isogai, A. J. Antibiot., 1997, 50, 111-118.
4. Sakuda, S.; Ono, M.; Furihata, K.; Nakayama, J.; Suzuki, A.; Isogai, A. J. Am. Chem. Soc., 1996, 118, 7855-7856.
5. Blasticidin A inhibited aflatoxin production in A. parasiticus at the concentration of 0.5 μg/mL completely without inhibiting its growth, which was the same activity as aflastatin A showed. The biological activity of blasticidin A as an inhibitor of aflatoxin production will be published in detail elsewhere.
6. D +10.8° (c 1.0, DMSO).
7. CH=8Hz): H-3 to C-1, 4, 5, 9 and 10, H-5 to C-3, 4, 6 and 10, H-7 to C-5, 6, 8 and 11, H-8 to C-6 and 7, H-9 to C-1, 2 and 3, H-10 to C-3, 4 and 5, H-11 to C-5, 6 and 7, H-5′ to C-2′ and 4′, H-6′ to C-2′ and 5′.
8. CH=8Hz): H-1 to C-2, 3 and 18, H-2 to C-18, H-3 to C-1, 2, 4 and 5, H-5 to C-6, H-6 to C-19, H-7 to C-5, 6, 8, 9 and 20, H-8 to C-20, H-9 to C-7, 8, 10, 11 and 20, H-11 to C-9, 10, 12 and 13, H-13 to C-11, 12, 14 and 15, H-15 to C-14, 16 and 17, H-17 to C-15 and 16, H-18 to C-1, 2 and 3, H-19 to C-5, 6 and 7, H-20 to C-7, 8 and 9.
9. 3OD, 500MHz) 180.8(C-1), 70.4(C-3), 45.4(C-2), 38.0(C-4), 33.1(C-11), 30.8, 30.5 and 26.7(C-5,6,7,8,9,10), 23.7(C-12), 14.4(C-13).
10. Ovchinnikov, Y. A.; Ivanov, V. T.; Kostetsky, P. V.; Shemyakin, M. M. Tetrahedron Lett., 1966, 43, 5285-5290.