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- W2313185178 abstract "Cyclic structures can increase the proteolytic stability and conformational rigidity of peptides, and N-alkylation of the peptide backbone can make peptides more cell-permeable and resistant to proteolysis. Therefore, cyclic N-alkyl amino acids are expected to be useful building blocks to increase simultaneously these pharmacological properties of peptides. In this study, we screened various cyclic N-alkyl amino acids for their ribosomal incorporation into peptides and identified cyclic N-alkyl amino acids that can be efficiently and successively incorporated. We also demonstrated genetic code reprogramming for reassigning 16 NNU codons to 16 different cyclic N-alkyl amino acids with high fidelity to synthesize highly N-alkylated polycyclic peptidomimetics and an mRNA-displayed library of completely N-alkylated polycyclic peptidomimetics by using our recently developed TRAP (transcription/translation coupled with association of puromycin linker) display. In vitro selection from a highly diverse library of such completely N-alkylated polycyclic peptidomimetics could become a powerful means to discover small-molecule ligands such as drug candidates that can be targeted to biomolecules inside living cells." @default.
- W2313185178 created "2016-06-24" @default.
- W2313185178 creator A5010970429 @default.
- W2313185178 creator A5048264434 @default.
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- W2313185178 date "2013-08-08" @default.
- W2313185178 modified "2023-10-04" @default.
- W2313185178 title "Extensive Reprogramming of the Genetic Code for Genetically Encoded Synthesis of Highly N-Alkylated Polycyclic Peptidomimetics" @default.
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- W2313185178 doi "https://doi.org/10.1021/ja405044k" @default.
- W2313185178 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23899321" @default.
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