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N-Substituted Glycines with Functional Side-Chains for Peptoid Synthesis

Authors :
Jean Martinez
Florine Cavelier
Adeline René
Source :
European Journal of Organic Chemistry. 2014:8142-8147
Publication Year :
2014
Publisher :
Wiley, 2014.

Abstract

N-Substituted glycines (NSG) constitute mimics of natural amino acids, and bring stability to peptide analogues. We developed a method to synthesize NSG bearing reactive secondary heterofunctionality. It was shown that persilylation could be used for temporary protection of reactive groups present on the substrate, with the aim of selectively alkylating the amine groups. NSG ready for peptide coupling were obtained by C-terminal deprotection and N-terminal protection of the resulting amino acid derivatives. This method was applied to prepare N-alkylated glycines as analogues of serine, cysteine, tyrosine and tryptophan. The last two derivatives were obtained in good yields and N-homotyrosine (N-hTyr) has been introduced into a peptide sequence of interest using automated solid-phase peptide synthesis (SPPS).

Details

ISSN :
1434193X
Volume :
2014
Database :
OpenAIRE
Journal :
European Journal of Organic Chemistry
Accession number :
edsair.doi...........58193f9b44a4a52f757a56d9a9161cbb
Full Text :
https://doi.org/10.1002/ejoc.201402864