A new efficient synthesis of acetyltelluro- and acetylselenomethionine and their use in the biosynthesis of heavy-atom protein analogs

Journal of the American Chemical Society

Volumn 118, Issue 4, 1996, Pages 913-914

  Karnbrock, Wilhelm ^a   Weyher, Elisabeth ^a   Budisa, Nediljko ^a   Huber, Robert ^a   Moroder, Luis ^a  

^a MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSELENOMETHIONINE; ACETYLTELLUROMETHIONINE; LIPOCORTIN 5; METHIONINE DERIVATIVE; ORGANOSELENIUM DERIVATIVE; ORGANOTELLURIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STABILITY; DRUG SYNTHESIS; ENANTIOMER; ESCHERICHIA COLI; MASS SPECTROMETRY; PROTEIN SYNTHESIS;

EID: 0030020116     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953222j     Document Type: Article

References (34)

1. Cowie, D. B.; Cohen, G. N. Biochim. Biophys. Acta 1957, 26, 252.
2. Boles, J. O., Lewinski, K.; Kunke, M.; Odom, J. D.; Dunlap, B. R.; Lebioda, L.; Hatada, M. Nat. Struct. Biol. 1994, 1, 283.
3. Budisa, N.; Steipe, B.; Demange, P.; Eckerskorn, C.; Kellermann, S., Huber, R. Eur. J. Biochem 1995, 230, 788.
4. Green, D. W., Ingram, V. M.; Perutz, M F. Proc. R. Soc. London 1954, A225, 287.
5. (a) Hendrickson, W. A.; Horton, J.; LeMaster, D. EMBO J. 1990, 9, 1665.
6. (b) Hendrickson, W. A. Science 1991, 254, 51.
7. Reinemer, P ; Prade, L.; Hof, P.; Neuefeind, T.; Huber, R., Zettl, R.; Palme, K., Schell, J ; Koelln, I.; Bartunik, H. D., Bieseler, B. J. Mol. Biol., submitted.
8. (a) Painter, E. P. J. Am. Chem. Soc. 1947, 69, 232.
9. (b) Plieninger, H. Chem Ber. 1950, 83, 265.
10. (c) Zdansky, G. Ark. Kemi 1968, 29, 437.
11. (d) Barton, D. H. R., Bridon, D.; Hervé, Y.; Potier, P.; Thierry, J., Zard, S. Z. Tetrahedron 1986, 42, 4983.
12. (e) Krief, A.; Trabelsi, M Synth. Commun. 1989, 19, 1203.
13. (f) Esaki, N., Shimoi, H.; Soda, Y.-S. Biotechnol. Appl. Biochem. 1989, 11, 312.
14. (g) Koch, T.; Buchardt, O. Synthesis 1993, 1065.
15. Knapp, F. F. J. Org. Chem. 1979, 44, 1007.
16. Silks, L. A.; Boles, J. O.; Modi, B. P.; Dunlap, R. B.; Odom, J. D. Synth. Commun. 1990, 20, 1555.
17. (a) Snyder, H. R.; Andreen, J. H., Cannon, G. W.: Peters, C. F. J. Am. Chem. Soc. 1942, 64, 2082
18. (b) Fillman, J.; Albertson, N. J Am. Chem. Soc. 1948, 70, 171.
19. Evers, M. J.; Christiaens, L. E ; Renson, M. J. J Org. Chem. 1986, 51, 5196
20. (a) McMurray, J. Org. React 1976, 24, 187.
21. (b) Chen, J.; Zhou, X. J. Synthesis 1987, 586.
22. (c) Li, W.; Zou, X. J.; Ma, Q. Synth. Commun. 1995, 25, 553.
23. (d) Liotta, D ; Sunay, U., Santiesteban, H.; Markiewicz, W. J. Org. Chem. 1981, 46, 2605.
24. (a) Birnbaum, S. M.; Levintow, L.; Kingsley, R. B., Greenstein, J. P. J. Biol. Chem. 1952, 194, 455.
25. (b) Greenstein, J. P. Methods Enzymol. 1957, 3, 554.
26. (c) Chibata, I.; Tosa, T.; Sato, T ; Mori, T. Methods Enzymol. 1976, 44, 746.
27. (d) Chenault, H. K.; Dahmer, J.; Whitesides. G M J. Am. Chem. Soc. 1989, 111, 6354.
28. (a) Reichel, L.; Kirschbaum, E. Liebigs Ann. Chem 1936, 523, 211.
29. (b) Balfe, M. P.; Chaplin, C. A.; Phillips, H J. Chem. Soc 1938, 341
30. (c) Balfe, M. P ; Nandl, K. N. J Chem. Soc. 1941, 70.
31. (d) Detty, M. R. J. Org. Chem. 1980, 45, 274.
32. (e) Kirsch, G.; Goodman, M M., Knapp, F. F Organometallics 1983, 2, 357.
33. (a) Detty, M. R ; Friedman, A. F.; Oseroff, A. R. J. Org. Chem. 1994, 59, 8245.
34. (b) Engman, L.; Stern, D.; Pelcman, M.; Andersson, C. M. J. Org. Chem. 1994, 59, 1973.