Syntheses of racemic and non-racemic silicon- and germanium-containing α-amino acids of the formula type H2NCH(CH2ElR3)COOH (El=Si, Ge; R=organyl) and incorporation of D-H2NCH(CH2SiMe3)COOH and D-H2NCH(CH2GeMe3)COOH into biologically active decapeptides: A study on C/Si/Ge bioisosterism

Journal of Organometallic Chemistry

Volumn 628, Issue 2, 2001, Pages 183-194

  Merget, Markus ^a   Günther, Kurt ^b   Bernd, Michael ^c   Günther, Eckhard ^c   Tacke, Reinhold ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b Infracor GmbH   (Germany)

^c ASTA MEDICA AG   (Germany)

Author keywords

Amino acids; C Si Ge bioisosterism; Germanium; GnRH antagonists; Peptides; Silicon

Indexed keywords

EID: 18044403017     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)00783-5     Document Type: Article

References (31)

1. Reviews dealing with bioorganosilicon and bioorganogermanium chemistry: (a) R. Tacke, H. Linoh, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Organic Silicon Compounds, Part 2, Wiley, Chichester, 1989, pp. 1143-1206.
2. (b) E. Lukevics, L. Ignatovich, Appl. Organomet. Chem. 6 (1992) 113.
3. (c) R. Tacke, S.A. Wagner, in: Z. Rappoport, Y. Apeloig (Eds.), The Chemistry of Organic Silicon Compounds, vol. 2, Part 3, Wiley, Chichester, 1998, pp. 2363-2400.
4. (d) R. Tacke, T. Heinrich, T. Kornek, M. Merget, S.A. Wagner, J. Gross, C. Keim, G. Lambrecht, E. Mutschler, T. Beckers, M. Bernd, T. Reissmann, Phosphorus, Sulfur, and Silicon 150/151 (1999) 69.
5. Merget M., Bartoschek S., Willeke R., Tacke R. Auner N., Weis J. Organosilicon Chemistry IV - From Molecules to Materials. 2000;33-36 Wiley-VCH, Weinheim.
6. Handmann V.I., Merget M., Tacke R. Z. Naturforsch. B. 55:2000;133.
7. Tacke R., Merget M., Bertermann R., Bernd M., Beckers T., Reissmann T. Organometallics. 19:2000;3486.
8. (a) L. Birkofer, A. Ritter, Angew. Chem. 68 (1956) 461.
9. (b) L. Birkofer, A. Ritter, Liebigs Ann. Chem. 612 (1958) 22.
10. Porter T.H., Shive W. J. Med. Chem. 11:1968;402.
11. Fitzi R., Seebach D. Tetrahedron. 44:1988;5277.
12. Weidmann B. Chimia. 46:1992;312.
13. Walkup R.D., Cole D.C., Whittlesey B.R. J. Org. Chem. 60:1995;2630.
14. Yamanaka H., Fukui T., Kawamoto T., Tanaka A. Appl. Microbiol. Biotechnol. 45:1996;51.
15. Myers A.G., Gleason J.L., Yoon T., Kung D.W. J. Am. Chem. Soc. 119:1997;656.
16. Smith R.J., Bratovanov S., Bienz S. Tetrahedron. 53:1997;13695.
17. Sibi M.P., Harris B.J., Shay J.J., Hajra S. Tetrahedron. 54:1998;7221.
18. Ishikawa H., Yamanaka H., Kawamoto T., Tanaka A. Appl. Microbiol. Biotechnol. 53:1999;19.
19. C. Bolm, A. Kasyan, K. Drauz, K. Günther, G. Raabe, Angew. Chem. 112 (2000) 2374; Angew. Chem. Int. Ed. 39 (2000) 2288.
20. C. Bolm, A. Kasyan, K. Drauz, K. Günther, G. Raabe, Angew. Chem. 112 (2000) 2374; Angew. Chem. Int. Ed. 39 (2000) 2288.
21. (a) B. Kutscher, M. Bernd, T. Beckers, E.E. Polymeropoulos, J. Engel, Angew. Chem. 109 (1997) 2240; Angew. Chem. Int. Ed. 36 (1997) 2148.
22. (a) B. Kutscher, M. Bernd, T. Beckers, E.E. Polymeropoulos, J. Engel, Angew. Chem. 109 (1997) 2240; Angew. Chem. Int. Ed. 36 (1997) 2148.
23. (b) T. Reissmann, J. Engel, B. Kutscher, M. Bernd, P. Hilgard, M. Peukert, I. Szelenyi, S. Reichert, D. Gonzales-Barcena, E. Nieschiag, A.M. Comaru-Schally, A.V. Schally, Drugs of the Future 19 (1994) 228.
24. M. Bernd, B. Kutscher, E. Günther, P. Romeis, T. Reissmann, T. Beckers, DE 199 11 771.3, PCT/EP 2000/02165.
25. Haviv F., Fitzpatrick T.D., Nichols C.J., Swenson R.E., Mort N.A., Bush E.N., Diaz G., Nguyen A.T., Holst M.R., Cybulski V.A., Leal J.A., Bammert G., Rhutasel N.S., Dodge P.W., Johnson E.S., Cannon J.B., Knittle J., Greer J. J. Med. Chem. 36:1993;928.
26. Trost B.M. Science. 254:1991;1471.
27. J.M. Stewart, J.D. Young, Solid-Phase Peptide Synthesis, Pierce Chemical Co, Rockford, USA, 1984.
28. U. Groth, T. Huhn, B. Porsch, C. Schmeck. U. Schöllkopf, Liebigs Ann. Chem. (1993) 715.
29. Tacke R., Becker B. J. Organomet. Chem. 354:1988;147.
30. Seyferth D., Rochow E.G. J. Am. Chem. Soc. 77:1955;907.
31. Altamura M., Giammaruco M, Taddei M., Ulivi P. J. Org. Chem. 60:1995;8403.