Organic & Biomolecular Chemistry Blog

Researchers in Canada have developed the first benzimidazolium-based synthetic ion channel and shown that it can cause damage to bacterial cells walls.

The movement of ions through cell walls is essential for a host of biological processes. The vast majority of this transportation occurs through ion channels or pores in the cell membrane. Man-made versions of these intracellular transport systems have been the subject of investigation by the supramolecular chemistry community for many years.

In this HOT paper, the Schmitzer group at the Université de Montréal are particularly interested in the transport of chloride ions in epithelial cells through calcium activated ion channels. They hope to mediate the concentrations of both calcium and chloride ions using synthetic ionophores.

Building on their research into imidazolium amphiphiles, they have developed a benzimidazolium-based compound that increases chloride flux in a variety of lipid bilayer systems, and increases bacterial cell wall permeability to calcium ions.

This compound will hopefully inspire new drugs to treat cystic fibrosis, which is caused by mutation of a chloride-ion channel known as the cystic fibrosis transmembrane conductance regulator protein (CFTR). They may also aid in the development of new antibiotics to combat resistant strains of bacteria.

Want to find out more? Read this paper FREE for the next 4 weeks.

Benzimidazolium-based synthetic chloride and calcium transporters in bacterial membranes
Claude-Rosny Elie, Audrey Hébert, Mathieu Charbonneau, Adam Haiun and Andreea R. Schmitzer
DOI: 10.1039/C2OB26966J

Published on behalf of Annabella Newton, Organic & Biomolecular Chemistry web science writer. Annabella Newton is a postdoctoral researcher based in Melbourne, Australia.

In this HOT communication Boris J. Nachtsheim and colleagues at Eberhard Karls University present preliminary results towards a fast and efficient synthetic approach of γ-spirolactams based on an iodine(III)-mediated oxidative spirocyclization of 2-(4-hydroxybenzamido)-acrylates.

In addition Nachtsheim et al. discuss the discovery of an unexpected side reaction, a rare iodine(III)-mediated spirocyclization that gave δ-spirolactones. With fluorinated solvents and modified reaction conditions this side reaction was able to produce δ-spirolactones in yields up to 70%.

Interested? Find out more about these reactions and their mechanisms by downloading this Communication for FREE.

A hypervalent iodine-mediated spirocyclization of 2-(4-hydroxybenzamido)acrylates – unexpected formation of δ-spirolactones
Christian Hempel, Nicole M. Weckenmann, C. Maichle-Moessmer and Boris J. Nachtsheim
DOI: 10.1039/C2OB26815A

In this HOT communication Marvin H. Caruthers and co-workers from the University of Colorado show that oligodeoxyribonucleotides bearing boranephosphonate linkages (bpDNA) are able to reduce a variety of metal ions whilst producing nanoparticles. Carauthers et al. discovered that during the reduction of metal ions in protic solvents, the B–P bond undergoes solvolysis and generates phosphate diesters (in water) or triesters (in alcohols).

To highlight the utility of this reaction Caruthers et al. synthesised an oligomer containing an O-methyl phosphate triester linkage, which cannot be prepared via usual methods of DNA synthesis as such triesters are base labile.

Caruthers et al. believe that, in addition to bpDNA‘s potential applications in the construction of DNA templated metallic nanostructures, the new reactivity of boranephosphonates shown can be exploited as a general method for the introduction of a variety of functionalities onto the DNA backbone via phosphate triesters.

Intrigued? Read this Communication for free for the next 4 weeks to find out more!

This Communication is part of the Nucleic acids: new life, new materials collection. Why not take a look at similar work and let us know what you think here on the blog or on Twitter.

Reduction of metal ions by boranephosphonate DNA
Subhadeep Roy, Magdalena Olesiak, Petra Padar, Heather McCuen and Marvin H. Caruthers
DOI: 10.1039/C2OB26661J