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Peptoids bearing tertiary amino residues in the n-alkyl side chains: synthesis of a potent inhibitor of Semaphorin 3A |
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| Authors: | Joaquim Messeguer Marisol Montolio Eduardo Soriano Angel Messeguer |
| Institution: | a Department of Chemical and Biomolecular Nanotechnology, Institut de Química Avançada de Catalunya (IQAC-CSIC), J. Girona 18, E-08034 Barcelona, Spain b Institut de Bioenginyeria de Catalunya (IBEC). Parc Cientific de Barcelona, Barcelona, Spain c CMBNN group, Department of cell Biology, Faculty of Biology University of Barcelona, Barcelona, Spain d IRB Barcelona, Department of Cell Biology, University of Barcelona, Spain e CIBERNED (ISCIII), Barcelona Science Park, Baldiri Reixac 10, E-08028 Barcelona, Spain |
| Abstract: | 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 |
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