Other Peptide Modifications by DCR

In order to introduce reactive azides/alkynes in peptides, the Rutjes group utilized alcalase mediated dipeptide synthesis with amino add amides and either acetylenic or azido amino 

Taillefumier et al. were the first to report on cyclic j8-peptoids and described macrocycles comprised of A-propargyl-j8-alanine oligomers 44. The cyclic tetramer was 

R = (6-n) hydrogens and n triazole-linked peptides with arbitrary attachment points 

17 a-Ethyny 1-estradiol was coupled to azide-substituted peptoid oligomers and the resulting estradiol-peptoid conjugates 62 were shown to displace 17j8-estradiol (E2) at the estrogen receptor in a competitive binding experiment (albeit with 25-fold reduced potency compared to E2).  

R = hydrophilic and hydrophobic groups Rand Pi = various side chains R = benzyl, pentyl 

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