Ribosomal Incorporation of Consecutive β-Amino Acids

Journal of the American Chemical Society
Takayuki Katoh, Hiroaki Suga

Abstract

Due to their unique characteristics, which are not shared by canonical α-peptides, peptides that contain stretches of consecutive β-amino acids are attractive scaffolds for novel peptide drugs and nanomaterials. Although ribosomal incorporation of single or nonconsecutive β-amino acids into peptides has previously been reported, the incorporation of consecutive β-amino acids has not yet been accomplished. This is primarily due to their incompatibility with the ribosomal translation system. Here, we took advantage of engineered β-aminoacyl-tRNAs bearing optimized T-stem and D-arm motifs for enhancing binding affinity to EF-Tu and EF-P, respectively. Combined with a reconstituted E. coli translation system and optimized translation factor concentrations, up to seven consecutive β-amino acids could be incorporated into a model peptide. Furthermore, the synthesis of macrocyclic β-peptides closed by a thioether bond between two d-α-amino acids is also demonstrated. This represents the first example of the ribosomal synthesis of peptides containing stretches of consecutive β-amino acids.

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Citations

Jan 30, 2019·International Journal of Molecular Sciences·Takayuki Katoh, Hiroaki Suga
May 12, 2019·International Journal of Molecular Sciences·Ana CrnkovićDieter Söll
Jan 3, 2020·Angewandte Chemie·Christos TsiamantasHiroaki Suga
May 14, 2020·Chemical Communications : Chem Comm·Joongoo LeeMichael C Jewett
Jun 8, 2019·Chemical Communications : Chem Comm·Christos TsiamantasHiroaki Suga
Aug 15, 2020·Frontiers in Bioengineering and Biotechnology·Yang WuHao Qi
Nov 30, 2019·Nucleic Acids Research·Michael J HammerlingMichael C Jewett
Jun 25, 2020·Nature Communications·Anthony J QuartararoBradley L Pentelute
Apr 6, 2019·Chembiochem : a European Journal of Chemical Biology·Tomoshige FujinoHiroshi Murakami
Oct 30, 2020·Frontiers in Bioengineering and Biotechnology·Zhenling CuiKirill Alexandrov
Jan 8, 2021·Synthetic Biology·Michael J HammerlingMichael C Jewett
Jan 31, 2021·Nature Communications·Haruka TsutsumiHiroaki Suga
Feb 5, 2021·Nature Reviews. Drug Discovery·Markus MuttenthalerPaul F Alewood
Feb 17, 2021·Chemical Communications : Chem Comm·Joongoo LeeMichael C Jewett
Mar 28, 2021·Trends in Pharmacological Sciences·Hayden Peacock, Hiroaki Suga
Apr 7, 2021·Journal of the American Chemical Society·Sayaka ImanishiHiroaki Suga
May 23, 2021·Bioorganic & Medicinal Chemistry·Chao ZhangSidney M Hecht
Jun 18, 2021·Cell Systems·Camila KofmanMichael C Jewett
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wei WangDian Su
Jul 17, 2021·ACS Chemical Biology·Emel AdaligilWayne J Fairbrother
Sep 19, 2020·Journal of the American Chemical Society·Takayuki Katoh, Hiroaki Suga
Feb 16, 2019·Journal of the American Chemical Society·Alexander A VinogradovHiroaki Suga
Nov 11, 2020·ACS Combinatorial Science·Sabrina E IskandarAlbert A Bowers
Mar 5, 2020·Journal of the American Chemical Society·Takayuki Katoh, Hiroaki Suga
Oct 15, 2019·Biochemistry·Fred R WardJamie H D Cate
Nov 6, 2018·Chemical Reviews·Yichao HuangHiroaki Suga
Mar 24, 2020·RSC Chemical Biology·Manuel E Otero-RamirezHiroaki Suga
Sep 11, 2021·Accounts of Chemical Research·Yuki Goto, Hiroaki Suga
Nov 4, 2021·Journal of the American Chemical Society·Takayuki Katoh, Hiroaki Suga
Jul 2, 2021·Biochemistry·Mia A ShandellVirginia W Cornish

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