Synthesis of hybrid cyclopeptides through enzymatic macrocyclization

Emilia Oueis, Brunello Nardone, Marcel Jaspars, Nicholas J. Westwood, James H. Naismith

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Natural products comprise a diverse array of molecules many of which are biologically active. Most natural products derive from combinations of polyketides, peptides, sugars and fatty acid building blocks. Peptidic macrocycles have attracted attention as potential therapeutics possessing cell permeability, stability and easy to control variability. Here we show that enzymes from the patellamide biosynthetic pathway can be harnessed to make macrocycles that are hybrids of amino acids and a variety of man- made chemical building blocks, including aryl rings, polyethers and alkyl chains. We have made macrocycles with only three amino acids, one of which can be converted to a thiazoline or a thiazole ring. We report the synthesis of 18 peptide hybrid macrocycles, 9 of which have been isolated and fully characterized.
Original languageEnglish
Pages (from-to)11-14
Number of pages4
JournalChemistryOpen
Volume6
Issue number1
Early online date13 Dec 2016
DOIs
Publication statusPublished - 2 Feb 2017

Keywords

  • Biotransformation
  • Cyanobactin
  • Hybrid macrocycles
  • Macrocyclization
  • Peptides

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