Total structure determination of grassypetolide, a new marine cyanobacterical cytotoxin

Organic Letters

Volumn 10, Issue 5, 2008, Pages 789-792

  Kwan, Jason C ^a   Rocca, James R ^a   Abboud, Khalil A ^b   Paul, Valerie J ^c   Luesch, Hendrik ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b University of Florida

^c SMITHSONIAN MARINE STATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DEPSIPEPTIDE; GRASSYPEPTOLIDE;

ARTICLE; BIOLOGY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYANOBACTERIUM; DRUG SCREENING; HUMAN; IC 50; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; UNITED STATES; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; CYANOBACTERIA; DEPSIPEPTIDES; DRUG SCREENING ASSAYS, ANTITUMOR; FLORIDA; HUMANS; INHIBITORY CONCENTRATION 50; MARINE BIOLOGY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

EID: 43549124620     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702946d     Document Type: Article

References (29)

1. Gerwick, W. H.; Tan, L. T.; Sitachitta, N. Alkaloids Chem. Biol. 2001, 57, 75-184.
2. (a) Matthew, S.; Ross, C.; Rocca, J. R.; Paul, V. J.; Luesch, H. J. Nat. Prod. 2007, 70, 124-127.
3. (b) Taori, K.; Matthew, S.; Rocca, J. R.; Paul, V. J.; Luesch, H. J. Nat. Prod. 2007, 70, 1593-1600.
4. Kuffner, I. B.; Walters, L. J.; Becerro, M. A.; Paul, V. J.; Ritson-Williams, R.; Beach, K. S. Mar. Ecol. Prog. Ser. 2006, 323, 107-117.
5. (a) Fusetani, N.; Sugawara, T.; Matsunaga, S.; Hirota, H. J. Am. Chem. Soc. 1991, 113, 7811-7812.
6. (b) Kobayashi, J.; Itagaki, F.; Shigemori, H.; Ishibashi, M.; Takahashi, K.; Ogura, M.; Nagasawa, S.; Nakamura, T.; Hirota, H.; Ohta, T.; Nozoe, S. J. Am. Chem. Soc. 1991, 113, 7812-7813.
7. (c) Nakao, Y.; Fujita, M.; Warabi, K.; Matsunaga, S.; Fusetani, N. J. Am. Chem. Soc. 2000, 122, 10462-10463.
8. Tan, L. T.; Sitachitta, N.; Gerwick, W. H. J. Nat. Prod. 2003, 66, 764-771.
9. Wipf, P.; Fritch, P. C.; Geib, S. J.; Sefler, A. M. J. Am. Chem. Soc. 1998, 120, 4105 -4112.
10. (a) Schmidt, E. W.; Nelson, J. T.; Rasko, D. A.; Sudek, S.; Eisen, J. A.; Haygood, M. G.; Ravel, J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 7315-7320.
11. (b) Long, P. F.; Dunlap, W. C.; Battershill, C. N.; Jaspars, M. ChemBioChem 2005, 6, 1760-1765.
12. (c) Donia, M. S.; Hathaway, B. J.; Sudek, S.; Haygood, M. G.; Rosovitz, M. J.; Ravel, J.; Schmidt, E. W. Nat. Chem. Biol. 2006, 2, 729-735.
13. Collection site position: 24°43.381'N, 80°51.696'W.
14. Claridge, T. D. W. High-Resolution NMR Techniques in Organic Chemistry; Elsevier: San Diego, CA, 1999.
15. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596.
16. Only the 2R,3R and 2R,3S standards were used. The elution times of the 2S,3S and 2S,3R isomers were deduced by derivatizing these standards with DL-FDLA.
17. (a) Fujii, K.; Ikai, Y.; Mayumi, T.; Oka, H.; Suzuki, M.; Harada, K.-I. Anal. Chem. 1997, 69, 3346-3352.
18. (b) Fujii, K.; Ikai, Y.; Oka, H.; Suzuki, M.; Harada, K.-I. Anal. Chem. 1997, 69, 5146-5151.
19. Two peaks were observed corresponding to (2R,3R)- and (2S,3R)- Maba in the approximate ratio of 2.5:1. This is consistent with chromato-grams of the standards, which were obtained from the corresponding N-benzoylated-O-methyl esters. The latter also showed some epimerization at the 2-position during hydrolysis.
20. Marfey's adducts of N-Me-D-Phe and N-Me-L-Leu co-eluted; however, the relative intensity of the corresponding peak was reduced and N-Me-D-Glu was generated when stringent ozonolysis conditions (25°C) were employed. Thus, a N-Me-D-Phe residue was present in 1.
21. One methanol molecule was seen incorporated into the lattice. Upon drying, the crystals would quickly degrade, presumably due to methanol loss.
22. Schmitz, F. J.; Ksebati, M. B.; Chang, J. S.; Wang, J. L.; Hossain, M. B.; van der Helm, D.; Engel, M. H.; Serban, A.; Silfer, J. A. J. Org. Chem. 1989, 54, 3463-3472.
23. 3.
24. 2 φ -1.36 cos φ + 0.33; see: Vögeli, B.; Ying, J.; Grishaev, A.; Bax, A. J. Am. Chem. Soc. 2007, 129, 9377-9385.
25. Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J.; Corbett, T. H. J. Am. Chem. Soc. 2001, 123, 5418-5423.
26. Kuntz, I. D.; Thomason, J. F.; Oshiro, C. M. Methods Enzymol. 1989, 177, 159-204 and references therein.
27. In the X-ray structure-like family, the average number of distance constraints over 1 Å was 1.3, and the average energy was 17.507 kcal/mol. The other family had an average number of 7 distance constraint violations over 1 Å and the average energy of the structures was 30.052 kcal/mol.
28. Hawkins, C. J.; Lavin, M. F.; Marshall, K. A.; van den Brenk, A. L; Watters, D. J. J. Med. Chem. 1990, 33, 1634-1638.
29. Brey, W.; Edison, A. S.; Nast, R. E.; Rocca, J. R.; Saha, S.; Withers, R. S. J. Magn. Reson. 2006, 179, 290-293.