Symplocin A, a linear peptide from the bahamian cyanobacterium symploca sp. configurational analysis of N, N -dimethylamino acids by chiral-phase HPLC of naphthacyl esters

Journal of Natural Products

Volumn 75, Issue 3, 2012, Pages 425-431

  Molinski, Tadeusz F ^a,b   Reynolds, Kirk A ^a   Morinaka, Brandon I ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BACTERIAL PROTEIN; CATHEPSIN E; ESTER; ISOLEUCINE; SYMPLOCIN A; UNCLASSIFIED DRUG; VALINE;

ARTICLE; BAHAMAS; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CYANOBACTERIUM; IC 50; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PEPTIDE ANALYSIS; PROTEIN STRUCTURE; SPECTROSCOPY; STEREOISOMERISM;

BAHAMAS; CATHEPSIN E; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYANOBACTERIA; ESTERS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NAPHTHALENES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES;

SYMPLOCA;

EID: 84859013763     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200861n     Document Type: Article

References (29)

1. Linington, R. G.; Clark, B. R.; Trimble, E. E.; Almanza, A.; Ureña, L. D.; Kyle, D. E.; Gerwick, W. H. J. Nat. Prod. 2009, 72, 14-17
2. Luesch, H.; Moore, R. E.; Paul, V. J.; Mooberry, S. L.; Corbett, T. J. Nat. Prod. 2001, 64, 907-910
3. Kwan, J. C.; Eksioglu, E. A.; Liu, C.; Paul, V. J.; Luesch, H. J. Med. Chem. 2009, 52, 5732-5747
4. Simmons, T. L.; McPhail, K. L.; Ortega-Barría, E.; Mooberry, S. L.; Gerwick, W. H. Tetrahedron Lett. 2006, 47, 3387-3390
5. Pettit, G. R.; Kamano, Y.; Dufresne, C.; Cerny, R. L.; Herald, C. L.; Schmidt, J. M. J. Org. Chem. 1989, 54, 6005-6006
6. Pettit, G. R.; Kamano, Y.; Herald, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, J. M.; Baczynskyj, L.; Tomer, K. B.; Bontems, R. J. J. Am. Chem. Soc. 1987, 109, 6883-63885
7. Pettit, G. R.; Singh, S. B.; Hogan, F.; Lloyd-Williams, P.; Herald, D. L.; Burkett, D. D.; Clewlow, P. J. J. Am. Chem. Soc. 1989, 111, 5463-5465
8. Pitot, H. C.; McElroy, E. A.; Reid, J. M. Clin. Cancer Res. 1999, 5, 523-531
9. MacMillan, J. B.; Ernst-Russell, M. A.; de Ropp, J. S.; Molinski, T. F. J. Org. Chem. 2002, 67, 8210-8215
10. Dalisay, D. S.; Rogers, E. W.; Edison, A.; Molinski, T. F. J. Nat. Prod. 2009, 72, 732-738
11. Hutchinson, C. R. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 3010-3012
12. Marfey, P. Carlsberg. Res. Commun. 1984, 49, 591-596
13. Stahl, G. L.; Walter, R.; Smith, C. W. J. Org. Chem. 1978, 43, 2285-2286
14. Schmidt, U.; Riedl, B.; Haas, G.; Griesser, H.; Vetter, A.; Weinbrenner, S. Synthesis 1993, 216-220
15. Galeotti, N.; Poncet, J.; Chiche, L.; Jouin, P. J. Org. Chem. 1993, 58, 5370-5376
16. Hosseini, M.; Kringelum, H.; Murray, A.; Tonder, J. E. Org. Lett. 2006, 8, 2103-2106
17. Fujii, K.; Ikai, Y.; Mayumi, T.; Oka, H.; Suzuki, M.; Harada, K.-I. Anal. Chem. 1997, 69, 3346-3352
18. Bray, A. M.; Maej, N. J.; Valerio, R. M.; Campbell, R. A.; Geysen, H. M. J. Org. Chem. 1991, 56, 6659-6666
19. Bowman, R. E.; Stroud, H. H. J. Chem. Soc. 1950, 1322-1345
20. Muller, J.; Feifel, S. C.; Schmiederer, T.; Zocher, R.; Sussmuth, R. D. ChemBioChem 2009, 10, 323-328
21. Liang, Z.; Sorribas, A.; Sulzmaier, F. J.; Jimenez, J. I.; Wang, X.; Sauvage, T.; Yoshida, W. Y.; Wang, G.; Ramos, J. W.; Williams, P. G. J. Org. Chem. 2011, 76, 3635-3643
22. Rinehart, K. L.; Sakai, R.; Kishore, V.; Sullins, D. W.; Li, K. M. J. Org. Chem. 1992, 57, 3007-3013
23. Pettit, G. R.; Singh, S. B.; Hogan, F.; Lloyd-Williams, P.; Herald, D. L.; Burkett, D. D.; Clewlow, P. J. J. Am. Chem. Soc. 1989, 111, 5463-5465
24. Zuidi, N.; Hermann, C.; Herrmann, T.; Kalbacher, H. Biochem. Biophys. Res. Commun. 2008, 377, 327-330
25. Dalisay, D. S.; Rogers, E. W.; Edison, A.; Molinski, T. F. J. Nat. Prod. 2009, 72, 732-738
26. Boone, D. R.; Castenholz, R. W. In Bergey's Manual of Systematic Bacteriology, Vol. 1, 2 nd ed.; Springer: New York, 2001; p 541.
27. Ingram, V. M. J. Biol. Chem. 1953, 202, 193-201
28. Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809-10810
29. Honda, Y.; Ori, A.; Tsuchihashi, G. Bull. Chem. Soc. Jpn. 1987, 60, 1027-1036