700376-95-0Relevant academic research and scientific papers
Linear TMC-95-based proteasome inhibitors
Basse, Nicolas,Piguel, Sandrine,Papapostolou, David,Ferrier-Berthelot, Alexandra,Richy, Nicolas,Pagano, Maurice,Sarthou, Pierre,Sobczak-Thépot, Jo?lle,Reboud-Ravaux, Michele,Vidal, Jo?lle
, p. 2842 - 2850 (2008/02/07)
We have designed and evaluated 45 linear analogues of the natural constrained cyclopeptide TMC-95A. These synthetically less demanding molecules are based on the tripeptide sequence Y-N-W of TMC-95A. Structural variations in the amino acid side chains and
Synthesis of Macrocyclic Peptide Analogues of Proteasome Inhibitor TMC-95A
Berthelot, Alexandra,Piguel, Sandrine,Le Dour, Gwennael,Vidal, Joelle
, p. 9835 - 9838 (2007/10/03)
The synthesis of three constrained macrocyclic peptide analogues 1 of TMC-95A as potential proteasome inhibitors is described. The key step involves a Ni(O)-mediated macrocyclization of tripeptides 2 bearing halogenated aromatic side chains for the formation of the biaryl junction. In addition, an enantioselective preparation of L-7-bromotryptophan methyl ester 3 using a Corey-O'Donnell alkylation of the glycine benzophenone imine was achieved in good overall yield with very high ee (>85%) on a multigram scale.
