Journal
TETRAHEDRON
Volume 66, Issue 13, Pages 2444-2454Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.01.090
Keywords
Peptoids; N-Alkylglycine monomers; Solid-phase synthesis; Semaphorin inhibition; Axonal regeneration
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Funding
- Ministry of Science and Innovation [CTQ 2005-00995, SAF2008-00048]
- MICINN, Instituto Carlos Tercero and Generalitat de Catalunya [SGR2009-366]
- Fundacio Marato TV3
- Spanish Ministry of Education and Science [SAF2005-0171, BFU2008-3980]
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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. (C) 2010 Elsevier Ltd. All rights reserved.
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