Complete stereochemistry of neamphamide A and absolute configuration of the β-methoxytyrosine residue in papuamide B

Journal of Organic Chemistry

Volumn 70, Issue 17, 2005, Pages 6842-6847

  Oku, Naoya ^a   Krishnamoorthy, Ravi ^b   Benson, Alan G ^b   Ferguson, Robert L ^b   Lipton, Mark A ^b   Phillips, Lawrence R ^a   Gustafson, Kirk R ^a   McMahon, James B ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; CHROMATOGRAPHIC ANALYSIS; DEGRADATION; REACTION KINETICS; SPECTROSCOPIC ANALYSIS; STEREOCHEMISTRY;

DERIVATIZATION; NEAMPHAMIDE;

NITROGEN COMPOUNDS;

AMINE; GUANIDINE DERIVATIVE; HEPTANOIC ACID DERIVATIVE; NATURAL PRODUCT; NEAMPHAMIDE A; PAPUAMIDE B; PEPTIDE DERIVATIVE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID COMPOSITION; ARTICLE; COMPARATIVE STUDY; DEGRADATION; DERIVATIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STANDARD; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

DEPSIPEPTIDES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; PEPTIDES, CYCLIC; STEREOISOMERISM; TYROSINE;

EID: 23644457650     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0508853     Document Type: Article

References (28)

1. Oku, N.; Gustafson, K. R.; Cartner, L. K.; Wilson, J. A.; Shigematsu, N.; Hess, S.; Pannell, L. K.; Boyd, M. R.; McMahon, J. B. J. Nat. Prod. 2004, 67, 1407-1411.
2. (a) Zampella, A.; D'Auria, M. V.; Paloma, L. G.; Casapullo, A.; Minale, L.; Debitus, C.; Henin, Y. J. Am. Chem. Soc. 1996, 118, 6202-6209.
3. (b) D'Auria, M. V.; Zampella, A.; Paloma, L. G.; Minale, L.; Debitus, C.; Roussakis, C.; Le Bert, V. Tetrahedron 1996, 52, 9589-9596.
4. (c) Zampella, A.; Randazzo, A.; Borbone, N.; Luciani, S.; Trevisi, L.; Debitus, C.; D'Auria, M. V. Tetrahedron Lett. 2002, 43, 6163-6166.
5. Ford, P. W.; Gustafson, K. R.; McKee, T. C.; Shigematsu, N.; Maurizi, L. K.; Pannell, L. K.; Williams, D. E.; de Silva, E. D.; Lassota, P.; Allen, T. M.; Van Soest, R.; Andersen, R. J.; Boyd, M. R. J. Am. Chem. Soc. 1999, 121, 5899-5909.
6. Trevisi, L.; Bova, S.; Cargnelli, G.; Danieli-Betto, D.; Floreani, M.; Germinario, E.; D'Auria, M. V.; Luciani, S. Biochem. Biophys. Res. Commun. 2000, 279, 219-222.
7. (b) Trevisi, L.; Cargnelli, G.; Ceolotto, G.; Papparella, I.; Semplicini, A.; Zampella, A.; D'Auria, M. V.; Luciani, S. Biochem. Pharmacol. 2004, 68, 1331-1338.
8. (a) Liang, B.; Carroll, P. J.; Joullie, M. M. Org. Lett. 2000, 2, 4157-4160.
9. (b) Okamoto, N.; Hara, O.; Makino, K.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1353-1358.
10. (c) Acevedo, C. M.; Kogut, E. F.; Lipton, M. A. Tetrahedron 2001, 57, 6353-6359.
11. Thoen, J. C.; Morales-Ramos, A. I.; Lipton, M. A. Org. Lett. 2002, 4, 4455-4458.
12. (a) Guerlavais, V.; Carroll, P. J.; Joullie, M. M. Tetrahedron: Asymmetry 2002, 13, 675-680.
13. (b) Zampella, A.; Sorgente, M.; D'Auria, M. V. Tetrahedron: Asymmetry 2002, 13, 681-685.
14. (c) Zampella, A.; D'Auria, M. V. Tetrahedron: Asymmetry 2002, 13, 1237-1239.
15. (d) Turk, J. A.; Visbal, G. S.; Lipton, M. A. J. Org. Chem. 2003, 68, 7841-7844.
16. (a) Okamoto, N.; Hara, O.; Makino, K.; Hamada, Y. J. Org. Chem. 2002, 67, 9210-9215.
17. (b) Hansen, D. B.; Wan, X.; Carroll, P. J.; Joullié, M. M. J. Org. Chem. 2005, 70, 3120-3126.
18. Marphy, P. Carlsberg Res. Commun. 1984, 49, 591-596.
19. 3OD was used in NMR experiments prior to the mass measurement, it is possible that the mass observed was the molecular ion of 6.
20. Meyers, A. I.; Lawson, J. P. Tetrahedron Lett. 1982, 23, 4883-4886.
21. Hardy, P. M. Synthesis 1978, 290-291.
22. Huang, Y.; Dalton, D.; Carroll, P. J. J. Org. Chem. 1997, 62, 372-376.
23. Nagai, N.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853-1856.
24. Boger, D. L.; Zhou, J.; Borzilleri, R. M.; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054-2069.
25. Schöllkopf, U.; Groth, U.; Deng, C. Angew. Chem., Int. Ed. Engl. 1981, 20, 798-799.
26. Oxidation without using a buffered solution did not give OMeAsp.
27. In a preliminary GC-MS experiment using D- and L-N-Cbz-Asp dimethyl esters as the models, both compounds eluted approximately 5 min after the thermal gradient reached the maximum temperature limit of the Chirasil column (200 °C) with poor mutual separation. This suggested that other derivatization of the amino group instead of Cbz was required to improve the chromatographic behavior of the methylated OMeAsp derivatives.
28. 4 oxidation. For example, (R)-βOMe-L-Tyr yields (2S,3S)-OMeAsp via this oxidative degradation.