by Keyword: Solid-phase synthesis

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Messeguer, J., Masip, I., Montolio, M., del Rio, J. A., Soriano, E., Messeguer, A., (2010). Peptoids bearing tertiary amino residues in the n-alkyl side chains: synthesis of a potent inhibitor of Semaphorin 3A Tetrahedron , 66, (13), 2444-2454

A study on the preparation of N-alkylglycines (peptoids) that contain tertiary amino residues on the N-alkyl side chains is reported. The appropriate combination of the submonomer strategy with N-alkylglycine monomer couplings depending upon the structure of the N-alkyl side chain that must be incorporated into the peptoid is determinant for the efficiency of the synthetic pathway. The application of this strategy to the preparation of SICHI, an N-alkyglycine trimer containing tertiary amino residues in the three N-alkyl branches, and that has been identified as a potent Semaphorin 3A inhibitor, is presented.

Keywords: Peptoids, N-Alkylglycine monomers, Solid-phase synthesis, Semaphorin inhibition, Axonal regeneration