Skip to main content
Log in

Dipeptides with 3-(trimethylstannyl)alanine building blocks: synthesis, characterization, and reactivity

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

3-(Trimethylstannyl)alanine esters containing a free amino group react with different N-benzoyloxycarbonyl amino acids in the presence of N,N′-dicyclohexylcarbodiimide to yield new dipeptides with β-(trimethylstannyl)alanine building blocks. Reactions at the stannyl group were studied in more detail in two glycyl alaninates. Their reaction with Me3SnCl without solvent yields the chlorostannyl-substituted compounds. The glycyl alaninates react with two equivalents of bromine to give the dibromostannylated compounds.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Molloy KC (1989) Bioorganotin compounds. In: Hartley FR (ed) The chemistry of the metal–carbon bond, vol 5. Wiley, Chichester, p 465

  2. Ho BYK, Zuckermann JJ (1973) Inorg Chem 12:1552

    Article  CAS  Google Scholar 

  3. Pellerito L, Lo Guidice MT, Ruisi G, Bertazzi N, Barbieri R, Huber F (1976) Inorg Chim Acta 17:L21

    Article  CAS  Google Scholar 

  4. Pellerito L, Lo Giudice MT, Stocco GC, Donaldson JD, Grimes SM, Smith PJ (1985) Polyhedron 4:747

    Article  CAS  Google Scholar 

  5. Sandhu GK, Kaur G, Holecek J, Lycka AJ (1987) Organomet Chem 332:75

    Article  CAS  Google Scholar 

  6. Ruisi G, Lo Giudice MT (1991) Appl Organomet Chem 5:385

    Article  CAS  Google Scholar 

  7. Guli G, Gennaro G, Pellerito L, Stocco GC (1993) Appl Organomet Chem 7:407

    Article  CAS  Google Scholar 

  8. Mundus-Glowacki B, Huber F, Preut H, Ruisi G, Barbieri R (1992) Appl Organomet Chem 6:83

    Article  CAS  Google Scholar 

  9. Koch J, Huber F, Ruisi G, Barbieri R (1994) Appl Organomet Chem 8:113

    Article  CAS  Google Scholar 

  10. Nath M, Pokharia S, Song X, Eng G, Gielen M, Kemmer M, Biesemans M, Willem R, de Vos D (2003) Appl Organomet Chem 17:305

    Article  CAS  Google Scholar 

  11. Nath M, Pokharia S, Eng G, Song X, Kumar A, Gielen M, Willem R, Biesemans M (2004) Appl Organomet Chem 18:460

    Article  CAS  Google Scholar 

  12. Nath M, Singh H, Kumar P, Kumar A, Song X, Eng G (2009) Appl Organomet Chem 23:347

    Article  CAS  Google Scholar 

  13. Baul TSB (2008) Appl Organomet Chem 22:195

    Article  CAS  Google Scholar 

  14. Nath M (2008) Appl Organomet Chem 22:598

    Article  CAS  Google Scholar 

  15. Nath M, Singh H, Eng G, Song X (2008) Spectrochim Acta A 71:529

    Article  Google Scholar 

  16. Nath M, Pokharia S, Eng G, Song X, Kumar A (2004) Synth React Inorg Met-Org Chem 34:1689

    Article  CAS  Google Scholar 

  17. Klein J, Lebelt I, Borsdorf R (1996) J Prakt Chem 338:544

    Article  CAS  Google Scholar 

  18. Sandhu GK, Kaur G (1990) J Organomet Chem 388:63

    Article  CAS  Google Scholar 

  19. Deska J, Kazmaier U (2007) Angew Chem Int Ed 46:4570

    Article  CAS  Google Scholar 

  20. Wilbur DS, Hamlin DK, Srivastava RR, Burns HD (1993) Bioconjug Chem 4:574

    Article  CAS  Google Scholar 

  21. Dölling K, Hartung H, Schollmeyer D, Weichmann H (1991) Z Anorg Allg Chem 600:153

    Article  Google Scholar 

  22. Dölling K, Krug A, Hartung H, Weichmann H (1995) Z Anorg Allg Chem 621:63

    Article  Google Scholar 

  23. Dölling K, Merzweiler K, Wagner C, Weichmann H (1999) Z Naturforsch 54b:293

    Google Scholar 

  24. Huber F, Vornefeld M, Preut H, von Angerer E, Ruisi G (1992) Appl Organomet Chem 6:597

    Article  CAS  Google Scholar 

  25. Huber F, Barbieri R (1986) In: Cardarelli NF (ed) Tin as a vital nutrient: implication in cancer prophylaxis and other physiological processes. CRC, Boca Raton

    Google Scholar 

  26. Shehan JC, Hess GP (1955) J Am Chem Soc 77:1067

    Article  Google Scholar 

  27. Markowicz MW, Dembinski R (2004) Synthesis 1:80

    Google Scholar 

  28. Wrackmeyer B (1985) Ann Rep NMR Spectrosc 16:73

    Article  CAS  Google Scholar 

  29. Petrosyan VS (1977) Prog NMR Spectrosc 11:115

    Article  Google Scholar 

  30. van Koten G, Noltes JG (1976) Adv Chem Ser 157:275

    Article  Google Scholar 

  31. Jastrzebski JTBH, van Koten G, Noltes JG (1993) Adv Organomet Chem 35:241

    Article  CAS  Google Scholar 

  32. Dölling K, Krug A, Hartung H, Weichmann H (1996) Z Naturforsch 51b:619

    Google Scholar 

  33. Bergmann M, Zervas L (1932) Ber Dtsch Chem Ges 65:1192

    Article  Google Scholar 

  34. Richter F, Weichmann H (1994) J Organomet Chem 466:77

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Karin Dölling.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dölling, K. Dipeptides with 3-(trimethylstannyl)alanine building blocks: synthesis, characterization, and reactivity. Monatsh Chem 144, 729–734 (2013). https://doi.org/10.1007/s00706-012-0902-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0902-6

Keywords

Navigation