507
Views
4
CrossRef citations to date
0
Altmetric
Research Article

Synthesis and biological properties of C-terminal vinyl ketone pseudotripeptides

, , , &
Pages 560-564 | Received 29 Nov 2011, Accepted 10 Jan 2012, Published online: 01 Mar 2012

References

  • Ciechanover A. The ubiquitin-proteasome proteolytic pathway. Cell 1994;79:13–21.
  • Reed SI. The ubiquitin-proteasome pathway in cell cycle control. Results Probl Cell Differ 2006;42:147–181.
  • Brannigan JA, Dodson G, Duggleby HJ, Moody PC, Smith JL, Tomchick DR et al. A protein catalytic framework with an N-terminal nucleophile is capable of self-activation. Nature 1995;378:416–419.
  • Coux O, Tanaka K, Goldberg AL. Structure and functions of the 20S and 26S proteasomes. Annu Rev Biochem 1996;65:801–847.
  • Löwe J, Stock D, Jap B, Zwickl P, Baumeister W, Huber R. Crystal structure of the 20S proteasome from the archaeon T. acidophilum at 3.4 A resolution. Science 1995;268:533–539.
  • Groll M, Ditzel L, Löwe J, Stock D, Bochtler M, Bartunik HD et al. Structure of 20S proteasome from yeast at 2.4 A resolution. Nature 1997;386:463–471.
  • Marques AJ, Palanimurugan R, Matias AC, Ramos PC, Dohmen RJ. Catalytic mechanism and assembly of the proteasome. Chem Rev 2009;109:1509–1536.
  • Kisselev AF, Songyang Z, Goldberg AL. Why does threonine, and not serine, function as the active site nucleophile in proteasomes? J Biol Chem 2000;275:14831–14837.
  • Rock KL, Goldberg AL. Degradation of cell proteins and the generation of MHC class I-presented peptides. Annu Rev Immunol 1999;17:739–779.
  • Testa U. Proteasome inhibitors in cancer therapy. Curr Drug Targets 2009;10:968–981.
  • Ludwig A, Fechner M, Wilck N, Meiners S, Grimbo N, Baumann G et al. Potent anti-inflammatory effects of low-dose proteasome inhibition in the vascular system. J Mol Med 2009;87:793–802.
  • Orlowski RZ. The role of the ubiquitin-proteasome pathway in apoptosis. Cell Death Differ 1999;6:303–313.
  • Myung J, Kim KB, Crews CM. The ubiquitin-proteasome pathway and proteasome inhibitors. Med Res Rev 2001;21:245–273.
  • Moore BS, Eustáquio AS, McGlinchey RP. Advances in and applications of proteasome inhibitors. Curr Opin Chem Biol 2008;12:434–440.
  • Groll M, Götz M, Kaiser M, Weyher E, Moroder L. TMC-95-based inhibitor design provides evidence for the catalytic versatility of the proteasome. Chem Biol 2006;13:607–614.
  • Nazif T, Bogyo M. Global analysis of proteasomal substrate specificity using positional-scanning libraries of covalent inhibitors. Proc Natl Acad Sci USA 2001;98:2967–2972.
  • Furet P, Imbach P, Noorani M, Koeppler J, Laumen K, Lang M et al. Entry into a new class of potent proteasome inhibitors having high antiproliferative activity by structure-based design. J Med Chem 2004;47:4810–4813.
  • Hogan PC, Corey EJ. Proteasome inhibition by a totally synthetic β-lactam related to salinosporamide A and omuralide. J Am Chem Soc 2005;127:15386–15387.
  • Momose I, Umezawa Y, Hirosawa S, Iinuma H, Ikeda D. Structure-based design of derivatives of tyropeptin A as the potent and selective inhibitors of mammalian 20S proteasome. Bioorg Med Chem Lett 2005;15:1867–1871.
  • Kaiser M, Groll M, Renner C, Huber R, Moroder L. The core structure of TMC-95A is a promising lead for reversible proteasome inhibition. Angew Chem Int Ed Engl 2002;41:780–783.
  • Clerc J, Groll M, Illich DJ, Bachmann AS, Huber R, Schellenberg B et al. Synthetic and structural studies on syringolin A and B reveal critical determinants of selectivity and potency of proteasome inhibition. Proc Natl Acad Sci USA 2009;106:6507–6512.
  • Adams J. The development of proteasome inhibitors as anticancer drugs. Cancer Cell 2004;5:417–421.
  • Adams J. The proteasome: a suitable antineoplastic target. Nat Rev Cancer 2004;4:349–360.
  • Crawford LJ, Walker B, Irvine AE. Proteasome inhibitors in cancer therapy. J Cell Commun Signal 2011;5:101–110.
  • Bogyo M, McMaster JS, Gaczynska M, Tortorella D, Goldberg AL, Ploegh H. Covalent modification of the active site threonine of proteasomal β subunits and the Escherichia coli homolog HslV by a new class of inhibitors. Proc Natl Acad Sci USA 1997;94:6629–6634.
  • Marastoni M, Baldisserotto A, Canella A, Gavioli R, Risi CD, Pollini GP et al. Arecoline tripeptide inhibitors of proteasome. J Med Chem 2004;47:1587–1590.
  • Marastoni M, Baldisserotto A, Trapella C, Gavioli R, Tomatis R. P3 and P4 position analysis of vinyl ester pseudopeptide proteasome inhibitors. Bioorg Med Chem Lett 2006;16:3125–3130.
  • Baldisserotto A, Ferretti V, Destro F, Franceschini C, Marastoni M, Gavioli R et al. α,β-unsaturated N-acylpyrrole peptidyl derivatives: new proteasome inhibitors. J Med Chem 2010;53:6511–6515.
  • Fehrentz JA, Pothion C, Califano JC, Loffet A, Martinez J. Synthesis of chiral N-protected α-amino aldehydes by reduction of N-protected N-carboxyanhydrides (UNCAs). Tetrahedron Lett 1994;35:9031–9034.
  • Gavioli R, Vertuani S, Masucci MG. Proteasome inhibitors reconstitute the presentation of cytotoxic T-cell epitopes in Epstein-Barr virus-associated tumors. Int J Cancer 2002;101:532–538.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.