Synthesis of an NDPK phosphocarrier domain peptide containing a novel triazolylalanine analogue of phosphohistidine using click chemistry

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5604-5607

  Yang, Sung Hyun ^a   Lee, Dong Jun ^a   Brimble, Margaret A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; DRUG DERIVATIVE; HISTIDINE; NUCLEOSIDE DIPHOSPHATE KINASE; PEPTIDE; PHOSPHOHISTIDINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; METABOLISM; SYNTHESIS;

ALANINE; CATALYSIS; CLICK CHEMISTRY; HISTIDINE; MOLECULAR STRUCTURE; NUCLEOSIDE-DIPHOSPHATE KINASE; PEPTIDES;

EID: 80054693127     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202333u     Document Type: Article

References (35)

1. Cohen, P. Nat. Cell Biol. 2002, 4, E127-130
2. Attwood, P. V.; Piggott, M. J.; Zu, X. L.; Besant, P. G. Amino Acids 2007, 32, 145-156
3. Puttick, J.; Baker, E. N.; Delbaere, L. T. Biochim. Biophys. Acta, Proteins Proteomics 2008, 1784, 100-105
4. Cho, H. S.; Pelton, J. G.; Yan, D.; Kustu, S.; Wemmer, D. E. Curr. Opin. Struct. Biol. 2001, 11, 679-684
5. Besant, P. G.; Attwood, P. V.; Piggott, M. J. Curr. Protein Pept. Sci. 2009, 10, 536-550
6. Khorchid, A.; Ikura, M. Int. J. Biochem. Cell Biol. 2006, 38, 307-312
7. Bourret, R. B.; Silversmith, R. E. Curr. Opin. Microbiol. 2010, 13, 113-115
8. Stewart, R. C. Curr. Opin. Microbiol. 2010, 13, 133-141
9. Hultquist, D. E. Biochim. Biophys. Acta 1968, 153, 329-340
10. Schenkels, C.; Erni, B.; Reymond, J. L. Bioorg. Med. Chem. Lett. 1999, 9, 1443-1446
11. Kee, J. K.; Villani, B.; Carpenter, A. R; Muir, T. W. J. Am. Chem. Soc. 2010, 132, 14327-14329
12. McAllister, T. E.; Nix, M. G.; Webb, M. E. Chem. Commun 2011, 47, 1297-1299
13. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
14. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
15. Huisgen, R. Chem. Ber. 1967, 100, 2494-2507
16. Huisgen, R. Pure Appl. Chem. 1989, 61, 613-628
17. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015
18. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137
19. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68
20. Lutz, J. Angew. Chem., Int. Ed. 2007, 46, 1018-1018
21. Gilles, M.; Presecan, E.; Vonica, A.; Lascu, I. J. Biol. Chem. 1991, 266, 8784-8789
22. Freije, J. M. P.; Blay, P.; MacDonald, N. J.; Manrow, R. E.; Steeg, P. S. J. Biol. Chem. 1997, 272, 5525-5532
23. Brunet, E.; Junanes, O.; Jimenez, L.; Rodriguez-Ubis, J. C. Tetrahedron Lett. 2009, 50, 5361-5563
24. Collet, S.; Bauchat, P.; Danion-Bougot, R.; Danion, D. Tetrahedron: Asymmetry 1998, 9, 2121-2131
25. Belokon', Y. N.; Tararov, V. I.; Maleev, V. I.; Savel'eva, T. F.; Ryzhov, M. G. Tetrahedon: Asymmetry 1998, 9, 4249-4252
26. Ueik, H.; Ellis, T. K.; Martin, C. H.; Boettiger, T. U.; Bolene, S. B.; Soloshonok, V. A. J. Org. Chem. 2003, 68, 7104-7107
27. Miller, N.; Williams, G. M.; Brimble, M. A. Org. Lett. 2009, 11, 2409-2412
28. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M. C. Tetrahedron Lett. 1977, 2, 155-158
29. Otaka, A.; Burke, T. R.; Smyth, M. S.; Nomizu, M.; Roller, P. Tetrahedron Lett. 1993, 34, 7039-7042
30. Salomon, C. J.; Breuer, E. Tetrahedron Lett. 1995, 36, 6759-6760
31. Jaureguiberry, C. G.; Ficheux, D.; Roques, B. P. Int. J. Protein Res. 1992, 39, 523-527
32. Green, O. M. Tetrahedron Lett. 1994, 35, 8081-8084
33. Yang, C.; Qamar, R.; Norton, S. J.; Cook, P. F. Tetrahedron Lett. 1994, 50, 1919-1926
34. Lee, D. J.; Harris, P. W. R.; Brimble, M. A. Org. Biomol. Chem. 2011, 9, 1621-1626
35. Alexandrova, L. A.; Skoblov, A. Y.; Jasko, M. V.; Victorova, L. S.; Krayevsky, A. A. Nucleic Acids Res. 1998, 26, 778-786