New research by MWC chemists rated very important

Co-authored by Dr Alan Cameron, Associate Professor Paul Harris and Distinguished Professor Dame Margaret Brimble, the paper reports a novel method of preparing allenamide-modified peptides - an unexplored functionality for peptides that provides a versatile chemical tool for effecting chemo-selective inter- or intramolecular bridging reactions with thiols.

The main finding, as described by first author Dr Cameron (pictured below) and the team, is that this new method is a valuable tool that can be used to constrain peptides to adopt a defined secondary structure - a technique that chemists can use to improve the biological activity of potential new drug targets.

Dr Alan Cameron, lead study author and research fellow in the Maurice Wilkins Centre and Brimble Lab, University of Auckland School of Chemical Sciences.

The journal notified the authors that their paper was rated HOT and the results, according to a referees' evaluation, 'very important' - a score achieved by less than 10% of the journal's manuscripts.

Paper selected for the cover

The paper was also selected for the back cover (pictured below) and the journal explained the artwork as follows:

"Chemoselective peptide modification tools are of continued interest in medicinal chemistry. We report methodology for the on-resin preparation of allenamide-modified peptides, thus enabling conjugation or intramolecular cyclisation via a thia-Michael addition. Here we represent this work with an allenamidyl-dog (peptide) catching an exogenous thiol-bearing stick or his own thiol-bearing tail, to afford a lipid conjugate or cyclic peptide respectively, both possessing the vinyl sulfide linkage shown amidst the mountain clouds of New Zealand's iconic Taranaki Maunga."

Citation:

Cameron AJ, Harris PWR, Brimble MA. On-resin preparation of allenamidyl peptides: a versatile chemoselective conjugation and intramolecular cyclisation tool. Angewandte chemie 2020; https://doi.org/10.1002/anie.202004656