Synthesis of fused tricyclic peptides using a reprogrammed translation system and chemical modification

Nasir Kato Bashiruddin; Masanobu Nagano; Hiroaki Suga

doi:10.1016/j.bioorg.2015.06.002

Synthesis of fused tricyclic peptides using a reprogrammed translation system and chemical modification

Bioorg Chem. 2015 Aug:61:45-50. doi: 10.1016/j.bioorg.2015.06.002. Epub 2015 Jun 20.

Authors

Nasir Kato Bashiruddin¹, Masanobu Nagano¹, Hiroaki Suga²

Affiliations

¹ Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
² Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. Electronic address: [email protected].

PMID: 26117092
DOI: 10.1016/j.bioorg.2015.06.002

Abstract

Here we report a unique method of ribosomally synthesizing fused tricyclic peptides. Flexizyme-assisted in vitro translation of a linear peptide with the N-terminal chloroacetyl group and four downstream cysteines followed by the addition of 1,3,5-tris(bromomethyl)benzene results in selective production of the fused tricyclic peptide. This technology can be used for the ribosomal synthesis of fused tricyclic peptide libraries for the in vitro selection of bioactive peptides with tricyclic topology.

Keywords: Cyclic peptides; Peptides; Translation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
DNA / metabolism
Molecular Sequence Data
Oligonucleotides / metabolism
Peptides, Cyclic / analysis
Peptides, Cyclic / biosynthesis*
Peptides, Cyclic / chemistry
Polymerase Chain Reaction
RNA, Transfer, Amino Acyl / metabolism
Ribosomes / metabolism
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

Oligonucleotides
Peptides, Cyclic
RNA, Transfer, Amino Acyl
DNA