Ribosomal Elongation of Cyclic γ-Amino Acids using a Reprogrammed Genetic Code.

Journal of the American Chemical Society
Takayuki Katoh, Hiroaki Suga

Abstract

Because γ-amino acids generally undergo rapid self-cyclization upon esterification on the carboxyl group, for example, γ-aminoacyl-tRNA, there are no reports of the ribosomal elongation of γ-amino acids to the best of our knowledge. To avoid such self-cyclization, we utilized cyclic γ-amino acids and demonstrated their elongation into a peptide chain. Although the incorporation of the cyclic γ-amino acids is intrinsically slow, we here show that the combination of elongation factor P and engineered tRNAs improves cyclic γ-amino acid incorporation efficiency. Via this method, thioether-macrocyclic peptides containing not only cyclic γ-amino acids but also d-α-, N-methyl-α-, and cyclic β-amino acids were expressed under the reprogrammed genetic code. Ribosomally synthesized macrocyclic peptide libraries containing cyclic γ-amino acids should be applicable to in vitro screening methodologies such as mRNA display for discovering novel peptide drugs.

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Citations

May 14, 2020·Chemical Communications : Chem Comm·Joongoo LeeMichael C Jewett
Jan 8, 2021·Synthetic Biology·Michael J HammerlingMichael C Jewett
Jan 31, 2021·Nature Communications·Haruka TsutsumiHiroaki Suga
Feb 17, 2021·Chemical Communications : Chem Comm·Joongoo LeeMichael C Jewett
Dec 16, 2020·Nature Reviews. Genetics·Daniel de la Torre, Jason W Chin
Jul 23, 2020·Cell Chemical Biology·Alexander A Vinogradov, Hiroaki Suga
Apr 7, 2021·Journal of the American Chemical Society·Sayaka ImanishiHiroaki Suga
Jun 18, 2021·Cell Systems·Camila KofmanMichael C Jewett
Jul 17, 2021·ACS Chemical Biology·Emel AdaligilWayne J Fairbrother
Sep 19, 2020·Journal of the American Chemical Society·Takayuki Katoh, Hiroaki Suga
Nov 20, 2020·Journal of the American Chemical Society·Yi TanXuechen Li
Nov 11, 2020·ACS Combinatorial Science·Sabrina E IskandarAlbert A Bowers
Sep 11, 2021·Accounts of Chemical Research·Yuki Goto, Hiroaki Suga

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