Regioselective α-Peptide Bond Formation Through the Oxidation of Amino Thioacids

Biochemistry
Ryo OkamotoYasuhiro Kajihara

Abstract

Biological systems, including ribosomes and enzymes, produce peptides with an extraordinary high speed and accuracy. On the other hand, a rational and regioselective α-peptide bond formation, without involving protecting groups, is difficult to achieve in chemical synthesis. In this study, α-amino thioacids were utilized for the generation of polypeptides without using any protecting groups. We found that an α-amino thioacid could oxidatively form a diaminoacyl-disulfide moiety and undergo a subsequent intramolecular S- to N-acyl transfer to form an α-peptide bond. Even the thioacid form of lysine, which has a free ε-amino group, generated a regioselective α-peptide bond. The oxidation of amino thioacids generated the oligomers of amino acids. Interestingly, this oligomerization reaction proceeded even in the presence of iron ore, a prebiotic element, thus suggesting a plausible prebiotic peptide bond forming reaction.

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Citations

Jul 12, 2019·Nature·Pierre CanavelliMatthew W Powner
Jul 31, 2019·Proceedings of the National Academy of Sciences of the United States of America·Moran Frenkel-PinterLoren Dean Williams
Feb 27, 2020·Chemical Reviews·Moran Frenkel-PinterLuke J Leman
Jul 1, 2021·Journal of the American Chemical Society·Kota NomuraYasuhiro Kajihara

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