A Direct Synthesis of 3,5-Dibromo-O-methyl-L-tyrosine

Synthetic Communications

Volumn 34, Issue 3, 2004, Pages 547-555

  Stewart, Jeremy ^a   Katsuyama, Isamu ^a   Fahmy, Hesham ^a   Fronczek, Frank R ^b   Zjawiony, Jordan K ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

3,5 Dibromo O methyl L tyrosine; Bromination; Bromotyrosine metabolite; Synthesis

Indexed keywords

3,5 DIBROMO O METHYLTYROSINE; BROMINE; HYDROCHLORIC ACID; METIROSINE; ORTHO METHYLTYROSINE; SOLVENT; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 1542346109     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120027296     Document Type: Article

References (37)

1. Pina, I.C.; Gautschi, J.T.; Wang, G.-Y.-S.; Sanders, M.L.; Schmitz, F.J. ; France, D.; Cornell-Kennon, S.; Sambucetti, L.C.; Remiszewski, S.W.; Perez, L.B.; Bair, K.W.; Crews, P. Psammaplins from the sponge Pseudoceratina purpurea: Inhibition of both histone deacetylase and DNA methyltransferase. J. Org. Chem. 2003, 68 (10), 3866-3873.
2. Tabudravu, J.N.; Jaspars, M. Purealidine S and purpuramine J, bromotyrosine alkaloids from the Fijian marine sponge Druinelia sp. J. Nat. Prod. 2002, 65 (12), 1798-1801.
3. Tsuda, M.; Endo, T.; Watanabe, K.; Fromont, J.; Kobayashi, J.; Nakirodin, A. A bromotyrosine alkaloid from a Verongid sponge. J. Nat. Prod. 2002, 65 (11), 1670-1671.
4. Saeki, B.M.; Granato, A.C.; Berlinck, R.G.S.; Magalhaes, A.; Schefer, A.B.; Ferreira, A.G.; Pinheiro, U.S.; Haidu, E. Two unprecedented dibromotyrosine-derived alkaloids from the Brazilian endemic marine sponge Aplysina caissara. J. Nat. Prod. 2002, 65 (5), 796-799.
5. Kijjoa, A.; Watanadilok, R.; Sonchaeng, P.; Silva, A.M.S.; Eaton, G.; Herz, W. 11, 17-Dideoxyagelorin A and B; new bromotyrosine derivates and analogs from the marine sponge Suberea aff. praetensa. Zeit. Naturforsch. C. J. Biosci. 2001, 56 (11/12), 1116-1119.
6. Fusetani, N.; Masuda, Y.; Nakao, Y.; Matsunaga, S.; van Soest, R.W.M. Three new bromotyrosine derivatives lethal to crab from the marine sponge, Pseudoceratina purpurea. Tetrahedron 2001, 57 (35), 7507-7511.
7. Sepcic, K.; Mancini, I.; Vidic, I.; Jovan, U.; Frassanito, R.; Pietra, F.; Macek, P.; Turk, T. Antibacterial and anticholinesterase activities of aplysamine-4, a bromotyrosine-derived metabolite of a Red Sea marine sponge. J. Nat. Toxins 2001, 10 (3), 181-191.
8. Takada, N.; Watanabe, R.; Suenaga, K.; Yamada, K.; Ueda, K.; Kita, M.; Uemura, D. Zamarnistatin A, significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea. Tetrahedron Lett. 2001, 42 (31), 5265-5267.
9. Tsuda, M.; Sakuma, Y.; Kobayashi, J. Suberedamines A and B, new bromotyrosine alkaloids from a sponge Suberea species. J. Nat. Prod. 2001, 64 (7), 980-982.
10. Nicholas, G.M.; Newton, G.L.; Fahey, R.C.; Bewley, C.A. Novel bromotyrosine alkaloids: inhibitors of mycothiol S-conjugate amidase. Org. Lett. 2001, 3 (10), 1543-1545.
11. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Magno, S. Chemistry of Verongida sponges, XI. Archerine, a novel anti-histaminic bromotyrosine-derived compound from the Caribbean marine sponge Aplysina archeri. Eur. J. Org. Chem. 2001 (1), 55-60.
12. Evan; T.; Rudi, A.; Ilan, M.; Kashman, Y.; Aplyzanzine, A. A new dibromotyrosine derivative from a Verongida sponge. J. Nat. Prod. 2001, 64 (2), 226-227.
13. Okamoto, Y.; Ojika, M.; Kato, S.; Sakagami, Y. Ianthesines A-D, four novel dibromotyrosine-derived metabolites from a marine sponge, lanthella sp. Tetrahedron 2000, 56 (32), 5813-5818.
14. Hirano, K.; Kubota, T.; Tsuda, M.; Watanabe, K.; Fromont, J.; Kobayashi, J. Ma'edamines A and B, cytotoxic bromotyrosine alkaloids with a unique 2(1H)pyrazinone ring from sponge Suberea sp. Tetrahedron 2000, 56 (41), 8107-8110.
15. Shin, J.; Lee, H.-S.; Seo, Y.; Rho, J.-R.; Cho, K.W.; Paul, V.J. New bromotyrosine metabolites from the sponge Aplysinella rhax. Tetrahedron 2000, 56 (46), 9071-9077.
16. Encarnacion, R.D.; Sandoval, E.; Malmstrom, J.; Christophersen, C. Calafianin, a bromotyrosine derivative from the marine sponge Aplysina gerardogreeni. J. Nat. Prod. 2000, 63 (6,) 874-875.
17. Compagnone, R.S.; Avila, R.; Suarez A.I., Abrams, O.V.; Rangel, H.R.; Arvelo, F.; Pina, I.C.; Merentes, E. 11-Deoxyfistularin-3, a new cytotoxic metabolite from the Caribbean sponge Aplysina fistularis insularis. J. Nat. Prod. 1999, 62 (10), 1443-1444.
18. Gao, H.; Kelly, M.; Hamann, M.T. Bromotyrosine-derived metabolites from the sponge Aiolochroia crassa. Tetrahedron 1999, 55 (32), 9717-9726.
19. Nicholas, G.M.; Eckman, L.L.; Newton, G.L.; Fahey, R.C.; Ray, S.; Bewley, C.A. Inhibition and kinetics of Mycobacterium tuberculosis and Mycobacterium smegmatis mycothiol-S-conjugate amidase by natural product inhibitors. Bioorg. Med. Chem. 2003, 11 (4), 601-608.
20. Rao, M. Rama; Venkatesham, U.; Sridevi, K.V.; Venkateswarlu, Y. Chemical constituents and their biological activities of the sponge family Aplysinellidae: a review. Indian J. Chem. B. Org. Chem. Med. Chem. 2000, 39B (10), 723-733.
21. Kim, D.; Lee, I.S.; Jung, J.H.; Yang, S.-I. Psammaplin A, a natural bromotyrosine derivative from a sponge, possesses the antibacterial activity against methicillin-resistant Staphylococcus aureus and the DNA gyrase-inhibitory activity. Arch. Pharm. Res. 1999, 22 (1), 25-29.
22. Koulman, A.; Proksch, P.; Ebel, R.; Beekman, A.C.; van Uden, W.; Konings, A.W.T.; Pedersen, J.A.; Pras, N.; Woerdenbag, H.J. Cytotoxicity and mode of action of aeroplysinin-1 and a related dienone from the sponge Aplysina aerophoba. J. Nat. Prod. 1996, 59 (6), 591-594.
23. Mack, M.M.; Molinski, T.F.; Buck, E.D.; Pessah, I.N. Novel modulators of skeletal muscle FKBP 12/calcium channel complex from Ianthella basta. Role of FKBP12 in channel gating. J. Biol. Chem. 1994, 296 (37), 23236-23249.
24. Nicholas, G.M.; Eckman, L.L.; Ray, S.; Hughes, R.O.; Pfefferkorn, J.A.; Barluenga, S.; Nicolaou, K.C.; Bewley, C.A. Bromotyrosine-derived natural and synthetic products as inhibitors of mycothiol-S-conjugate amidase. Bioorg. Med. Chem. Lett. 2002, 12 (17), 2487-2490.
25. Nicolaou, K.C.; Hughes, R.; Pfefferkorn, J.A.; Barluenga, S.; Roecker, A.J. Combinatorial synthesis through disulfide exchange: discovery of potent psammaplin a type antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA). Chem. Eur. J. 2001, 7 (19), 4280-4295.
26. Boehlow, T.R.; Harburn, J.J.; Spilling, C.D. Approaches to the synthesis of some tyrosine-derived marine sponge metabolites: synthesis of verongamine and purealidin N. J. Org. Chem. 2001, 66 (9), 3111-3118.
27. Wasserman, H.H.; Wang, J. Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin using the cyano ylide coupling methodology. J. Org. Chem. 1998, 63 (16), 5581-5586.
28. Murakata, M.; Tamura, M.; Hoshino, O. Asymmetric oxidative cyclization of O-phenolic oxime-esters: first synthesis of enantiomerically enriched spiroisoxazoline methyl esters. J. Org. Chem. 1997, 62 (13), 4428-4433.
29. Carney, J.R.; Rinehart, K.L. Biosynthesis of brominated tyrosine metabolites by Aplysina fistularis. J. Nat. Prod. 1995, 58 (7), 971-985.
30. Crowe, A.M.; Lawrie, K.W.M.; Saunders, D. The synthesis of [14C] and [3H2] SK&F L-94901. A novel thyromimetic. J. Labelled Compd. Radiopharm. 1988, 25, 763-772.
31. Nikolics, K.; Teplan, I.; Medzihradszky, K. Labeled polypeptides. V. Synthesis of α-melanotropin labeled with tritium on the tyrosine residue, via the dibromo intermediate. J. Labelled Compd. Radiopharm. 1976, 12 (2), 163-171.
32. Sano, S.; Ikai, K.; Katayama, K.; Takesako, K.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. 0F4949, new inhibitors of aminopeptidase B. II. Elucidation of structure. J. Antibiot. 1986, 36 (12), 1685-1696.
33. Akiyama, A.; Musso, G.F.; Smart, J.L.; Lang, C.; Straub, J.A. Bromination and subsequent catalytic tritiation of thienylalanine and 4-methyltyrosine residues in the bradykinin analog RMP-7. J. Labelled Compd. Radiopharm. 1994, 34 (12), 1217-1226.
34. Jung, M.E.; Rohloff, J.C. Organic chemistry of L-tyrosine. 1. General synthesis of chiral piperazines from amino acids. J. Org. Chem. 1985, 50 (24), 4909-4913.
35. Kroemer, R.T.; Liedl, K.R.; Dickinson, J.A.; Robertson, E.G.; Simons, J.P.; Borst, D.R.; Pratt, D.W. Conformationally induced changes in the electronic structures of some flexible benzenes. A molecular orbital model. J. Am. Chem. Soc. 1998, 120 (48), 12573-12582.
36. Andersh, B.; Murphy, D.L.; Olson, R.J. Hydrochloric acid catalysis of N-bromosuccinimide (NBS) mediated nuclear aromatic brominations in acetone. Synth. Commun. 2000, 30 (12), 2091-2098.
37. Tee, O.S.; Paventi, M.; Bennett, J.M. Kinetics and mechanism of the bromination of phenols and phenoxide ions in aqueous solution. Diffusion-controlled rates. J. Am. Chem. Soc. 1989, 111 (6), 2233-2240.