An Efficient Method for the In Vitro Production of Azol (in) e-Based Cyclic Peptides

Houssen, Wael E. and Bent, Andrew F. and McEwan, Andrew R. and Pieiller, Nathalie and Tabudravu, Jioji N. and Koehnke, Jesko and Mann, Greg and Adaba, Rosemary I. and Thomas, Louise and Hawas, Usama W. and Liu, Huanting and Schwarz-Linek, Ulrich and Smith, Margaret C. M. and Naismith, James H. and Jaspars, Marcel (2014) An Efficient Method for the In Vitro Production of Azol (in) e-Based Cyclic Peptides. Angewandte Chemie International Edition, 53 (51). pp. 14171-14174. ISSN 1521-3773

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Abstract

Heterocycle-containing cyclic peptides are promis-ing scaffolds for the pharmaceutical industry but their chemicalsynthesis is very challenging. A new universal method has beendevised to prepare these compounds by using a set ofengineered marine-derived enzymes and substrates obtainedfrom a family of ribosomally produced and post-translation-ally modified peptides called the cyanobactins. The substrateprecursor peptide is engineered to have a non-native proteasecleavage site that can be rapidly cleaved. The other enzymesused are heterocyclases that convert Cys or Cys/Ser/Thr intotheir corresponding azolines. A macrocycle is formed usinga macrocyclase enzyme, followed by oxidation of the azolinesto azoles with a specific oxidase. The work is exemplified by theproduction of 17 macrocycles containing 6–9 residues repre-senting 11 out of the 20 canonical amino acids

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science, Technology and Environment (FSTE) > School of Biological and Chemical Sciences
Depositing User:	Fulori Nainoca - Waqairagata
Date Deposited:	17 May 2017 21:44
Last Modified:	05 Jun 2017 02:41
URI:	http://repository.usp.ac.fj/id/eprint/9898

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