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Article Dans Une Revue European Journal of Organic Chemistry Année : 2014

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

Résumé

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 (NhTyr) has been introduced into a peptide sequence of interest using automated solid-phase peptide synthesis (SPPS).

Domaines

Chimie organique

Dates et versions

hal-01097178 , version 1 (19-12-2014)

Identifiants

Citer

Adeline René, Jean Martinez, Florine Cavelier. N-Substituted Glycines with Functional Side-Chains for Peptoid Synthesis.. European Journal of Organic Chemistry, 2014, 2014 (36), pp.8142-8147. ⟨10.1002/ejoc.201402864⟩. ⟨hal-01097178⟩
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