p‐Chloropropynyl Phenylalanine, a Versatile Non‐Canonical Amino Acid for Co‐Translational Peptide Macrocyclization and Side Chain Diversification

Author:

Osorio Franco H. Estheban12,Le Anthony V.12,Chang Nathan Y.12,Hartman Matthew C. T.12ORCID

Affiliation:

1. Chemistry Virginia Commonwealth University 1001 W Main St Richmond VA-23284 USA

2. Massey Cancer Center Virginia Commonwealth University 1001 W Main St Richmond VA-23284 USA

Abstract

AbstractMacrocyclization has proven to be a beneficial strategy to improve upon some of the disadvantages of peptides as therapeutics. Nevertheless, many peptide cyclization strategies are not compatible with in vitro display technologies like mRNA display. Here we describe the novel amino acidp‐chloropropynyl phenylalanine (pCPF). pCPF is a substrate for a mutant phenylalanyl‐tRNA synthetase and its introduction into peptides via in vitro translation leads to spontaneous peptide macrocyclization in the presence of peptides containing cysteine. Macrocyclization occurs efficiently with a wide variety of ring sizes. Moreover, pCPF can be reacted with thiols after charging onto tRNA, enabling the testing of diverse ncAAs in translation. The versatility of pCPF should facilitate downstream studies of translation and enable the creation of novel macrocyclic peptide libraries.

Funder

National Science Foundation

National Institutes of Health

Publisher

Wiley

Subject

Organic Chemistry,Molecular Biology,Molecular Medicine,Biochemistry

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