Synthesis of a novel histidine analogue and its efficient incorporation into a protein in vivo

Protein Engineering

Volumn 16, Issue 9, 2003, Pages 699-706

  Ikeda, Yutaka ^a,b   Kawahara, Shun Ichi ^b   Taki, Masumi ^b   Kuno, Atsushi ^b,c   Hasegawa, Tsunemi ^c   Taira, Kazunari ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c YAMAGATA UNIVERSITY   (Japan)

Author keywords

1,2,3 triazole; Amino acid analogue; Histidine; Incorporation; Translation

Indexed keywords

ALANINE DERIVATIVE; BETA (1,2,3 TRIAZOL 4 YL)ALANINE; HISTIDINE DERIVATIVE; HYDROGEN; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL STRAIN; BIOTECHNOLOGY; CONTROLLED STUDY; ESCHERICHIA COLI; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS; RNA TRANSLATION;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA;

EID: 0142215403     PISSN: 02692139     EISSN: None     Source Type: Journal    
DOI: 10.1093/protein/gzg084     Document Type: Article

References (25)

1. Adlington, R.M., Baldwin, J.A., Catterick, D. and Pritchard, G.J. (1999) J. Chem. Soc., Perkin Trans. 1, 855-866.
2. Aoyama, T., Sudo, K. and Shiori, T. (1982) Chem. Pharm. Bull. (Tokyo), 30, 3849-3851.
3. Arnez, J.G., Harris, D.C., Mitschler, A., Rees, B., Francklyn, C.S. and Moras, D. (1995) EMBO J., 14, 4143-4155.
4. Beiboer, S.H.W., van den Berg, B., Dekker, N., Cox, R.C. and Verheij, H.M. (1996) Protein Eng., 9, 345-352.
5. Brönsted, J.N. and Pedersen, K. (1923) Z. Phys. Chem. A, 108, 185.
6. Brown, H.C., Narasimhan, S. and Choi, Y.M. (1982) J. Org. Chem., 47, 4702-4708.
7. Corey, E.J. and Schmidt, G. (1979) Tetrahedron Lett., 20, 399-402.
8. Duncia, J.V., Pierce, M.E. and Santella, J.B., III (1991) J. Org. Chem., 56, 2395-2400.
9. Galburt, E.A., Chevalier, B., Tang, W., Jurica, M.S., Flick, K.E., Monnat, R.J., Jr and Stoddard, B.L. (1999) Nat. Struct. Biol., 6, 1096-1099.
10. Gray, C.J. (1971) Enzyme-catalyzed Reactions. Van Nostrand Reinhold, London, pp. 264-271.
11. Katritzky, A.R. and Rees, C.W. (1984) Comprehensive Heterocyclic Chemistry, Part 4A. Pergamon Press, Oxford.
12. Kochendoerfer, G.G. and Kent, S.B. (1999) Curr. Opin. Chem. Biol., 3, 665-671.
13. Koide, H., Yokoyama, S., Kawai, G., Ha, J.M., Oka, T., Kawai, S., Miyake, T., Fuwa, T. and Miyazawa, T. (1988) Proc. Natl Acad. Sci. USA, 85, 6237-6241.
14. Koide, H. et al. (1994) Biochemistry, 33, 7470-7476.
15. Liu, D.R. and Schultz, P.G. (1999) Proc. Natl Acad. Sci. USA, 96, 4780-4785.
16. Noren, C.J., Anthony-Cahill, S.J., Griffith, M.C. and Schultz, P.G. (1989) Science, 244, 182-188.
17. Omstein, P.L., Arnold, M.B., Evrard, D., Leander, J.D., Lodge, D. and Schoepp, D.D. (1993) Bioorg. Med. Chem. Lett., 3, 43-48.
18. Peracchi, A. (2001) Trends Biochem. Sci., 26, 497-503.
19. Ressler, C. and Ratzkin, H. (1961) J. Am. Chem. Soc., 26, 3356-3360.
20. Seyferth, D., Menzel, H., Dow, A.W. and Flood, T.C. (1972) J. Organomet. Chem., 279-290.
21. Sisido, M. and Hohsaka, T. (1999) Bull. Chem. Soc. Jpn., 72, 1409-1425.
22. Smith, M.B. (ed.) (1994) Organic Synthesis. McGraw-Hill, New York.
23. Soumillion, P. and Fastrez, J. (1998) Protein Eng., 11, 213-217.
24. van der Woerd, M.J., Pelletier, J.J., Xu, S.-Y. and Firedman, A.M. (2001) Structure, 9, 133-144.
25. van Hest, J.C.M., Kiick, K.L. and Tirrell, D.A. (2000) J. Am. Chem. Soc., 122, 1282-1288.