Structural identification of cepaciamide A, a novel fungitoxic compound from Pseudomonas cepacia D-202

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 1039-1042

  Jiao, Ying ^b   Yoshihara, Teruhiko ^b   Ishikuri, Shu ^a   Uchino, Hideaki ^a   Ichihara, Akitami ^b  

^a Research Center   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CEPACIAMIDE A; FUNGICIDE; UNCLASSIFIED DRUG;

ARTICLE; BURKHOLDERIA CEPACIA; CIRCULAR DICHROISM; DRUG ISOLATION; DRUG STRUCTURE; FUNGICIDAL ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030039269     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02342-9     Document Type: Article

References (15)

1. a) Ishikuri, S.; Uchino, H. and Kanzawa, K. Ann. Phytopath. Soc. Jpn. 1992, 58, 456-460.;
2. b) Tsuchiya K.; Homma Y., Komoto Y. and Suzui T.; Ann. Phytopath. Soc. Jpn. 1995, 61, 318-324.;
3. P. cepacia D-202 was deposited in the Fermentation Research Institute, Agency of Industrial Science and Technology Japan, under the accession number FERMP-11559.
4. a) Denmark, S. E. and Edwards, J. P. J. Org. Chem. 1991, 56, 6974-6981.;
5. b) Yamanoi, K. and Ohfune, Y. Tetrahedron Lett. , 1988, 29, 1181-1184.,
6. c) (formula presented)
7. Kaneshiro, T. and Marr, A. G. J . Biol. Chem. , 1961, 236, 2615-2614.
8. a) Ohtani, I. ; Kusumi, T. ; Ishitsuka, M. O. and Kakisawa, H. Tetrahedron Lett. 1989, 30, 3147.;
9. b) Difference of chemical shifts between (S)-MTPA and (R)-MTPA esters of 1c and 1b: (formula presented)
10. Pail, I. B. ; Trafford, C. ; Colin, D. and John, M. J. Chem. Soc. Perkin. 1, 1994, 1503-1508.
11. Pellegata, R. ; Pinza, M. and Pifferi, G. Synthesis, 1978, 614-616.
12. 3OD, multiplicities by DEPT) δ 11.23 (t), 14.28 (q), 16.15 (d), 23.05 (t), 23.38 (t), 25.30 (t), 25.62 (t), 27.58 (t), 29.14 (t), 29.61 (t), 29.74 (t), 29.97 (t), 30.10 (t), 30.56 (t), 30.65 (t), 32.34 (t), 35.02 (t), 35.36 (t), 39.69 (t), 42.68 (t), 54.37 (d), 70.69 (d), 72.95 (d), 170.78 (s), 175.41 (s), 176.71 (s).
13. 3); δ 14.12, 15.74, 22.70, 24.73, 28.70, 28.72, 29.30, 29.35, 29.46, 29.58, 29.62, 30.17, 30.19, 34.42, 52.48, 70.46, 173.26.
14. 3, mutiplicities by DEPT), δ 14.82 (q), 21.84 (t), 23.39 (t), 26.23 (t), 27.80 (t), 30.05 (t), 30.26 (t), 30.29 (t), 30.36 (t), 32.62 (t), 37.44 (t), 42.55 (t), 43.37 (t), 51.48 (d), 69.34 (d), 172.16 (s), 173.71(s).
15. 3OD); δ 1.22 (3H, d, J=5.9Hz), 1.67 (1H, m), 1.93 (2H, m), 2.25 (1H, m), 2.37 (2H, m), 3.47 (2H, m), 4.20 (1H, m), 4.39 (1H, m) ppm.