Archive for the ‘Subject Areas’ Category

Bioinspired catalysis for eco-friendly chemical transformations in water

One challenge that today’s chemists face is making large-scale processes more economical and environmentally friendly. Within this area, there has been a surge of interest in the development of bioinspired catalytic systems which, relative to traditional catalysis, have the potential to reduce chemical waste by 85% by performing efficient reactions in pure water.

Prof. Normand Voyer and coworkers from Laval University have recently published an eco-friendly methodology for the preparation of chiral a,b-epoxyketones in pure water using the supramolecular catalyst, homo-oligopeptide poly-L-leucine (PLL).

Achieving enantioselectivity in organic reactions carried out in water poses challenges but peptide derived catalysts have shown great promise in this regard. The best example of this is the Juliá-Colonna epoxidation which has been studied and improved since its discovery in the early 1980’s. While significant progress in this area has been made, most transformations using natural homo-oligopeptides have required the use of an organic co-solvent to improve reaction efficiency.

Professor Voyer shows the new, eco-friendly process begins with several homo-oligopeptides being synthesised from their corresponding amino acid N-carboxyanhydrides and used to catalyse the Juliá-Colonna epoxidation of an electron deficient olefin in water. Of all the catalysts, PLL provided the highest conversion and enantioselectivity (Table) however, the generality of the reaction appeared to be dependent on the sterics and electronics of the substrates.

Computational analysis was used to model the PLL supramolecular catalyst and rationalise the observed reaction trends. PLL adopts a helical conformation with hydrophobic grooves distributed along the helical axis. When modelled with substrate 1 (Table), it was observed that the chalcone moiety fits perfectly within the PLL groove and forms a stable complex. It is this complexation that also aids in solubility of the ketone, removing the need for an organic co-solvent.

Epoxidation is proposed to take place through a “groove sliding” mechanism, where the substrate slides into the hydrophobic pocket generated by the leucine side chains until it reaches the N-terminal of PLL where a hydroperoxide anion is waiting (Figure). This mechanistic proposal lends to the enantioselectivity of the reaction and explains the observed electronic and steric constraints.

While the scope of PLL remains limited, this study underscores the fact that conformation and the hydrophobic nature of the oligopeptide catalysts are critical for carrying out environmentally benign organic reactions and has set a precedent for the development of future biomimetic supramolecular catalysts.

To find out more see:

Revisiting the Juliá–Colonna enantioselective epoxidation: supramolecular catalysis in water
Christopher Bérubé, 
DOI:10.1039/C7CC01168G


Victoria Corless is currently completing her Ph.D. in organic chemistry with Prof. Andrei Yudin at The University of Toronto. Her research is centred on the synthesis of kinetically amphoteric molecules which offer a versatile platform for the development of chemoselective transformations with particular emphasis on creating novel biologically active molecules.

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Elizabeth New: Winner of the 2017 ChemComm Emerging Investigator Lectureship

On behalf of the ChemComm Editorial Board, we are delighted to announce Elizabeth New from the University of Sydney, Australia, as the winner of the 2017 ChemComm Emerging Investigator Lectureship – congratulations, Liz!

Elizabeth New

Liz finished her BSc (Advanced, Hons 1 and Medal) and MSc in Chemistry at the University of Sydney before embarking on a PhD programme at Durham University, UK, working with Professor David Parker. After being awarded her PhD in Chemistry in January, 2010, she was a Royal Commission for the Exhibition of 1851 Postdoctoral Fellow at the University of California at Berkeley within the group of Professor Christopher Chang. She then returned to the University of Sydney as an ARC DECRA Fellow to start her independent research career in 2012, establishing herself at the cutting-edge of molecular imaging and developing novel chemical imaging tools to supplement existing imaging platforms.

She developed the first set of reversible sensors for cellular redox environment containing flavins as the sensing group, including the first examples of ratiometric reversible cytoplasmic sensing, reversible mitochondrial sensing, and ratiometric mitochondrial sensing. She has also developed the first fluorescent sensor for a platinum metabolite, enabling the unprecedented visualisation of cisplatin metabolism, and a subsequent sensor to study the metabolism of transplatin analogues. Her research group is one of the very few in the world to be investigating cobalt complexes as responsive magnetic resonance contrast agents, and she has developed new methods for ratiometric fluorescent sensing, as well as new strategies to control subcellular targeting. Her research excellence has been recognised by a number of awards, among them the NSW Early Career Researcher of the Year (2016) and the Asian Biological Inorganic Chemistry Early Career Researcher Award (2014).

Passionate about communicating science, she has spoken about her research to high school students (as the Royal Australian Chemical Institute (RACI) Nyholm Youth Lecturer, 2014-5, and the RACI Tasmanian Youth Lecturer, 2017), to the general public (as a NSW Young Tall Poppy Awardee, 2015), and to politicians and policy-makers (as elected executive member of the Australian Academy of Science’s Early-Mid Career Researcher Forum). She is currently a Senior Lecturer and Westpac Research Fellow in the School of Chemistry at the University of Sydney, where her group continues to focus on the development of molecular probes for the study of biological systems.

As part of the Lectureship, Elizabeth will present a lecture at three locations over the coming year, with at least one of these events taking place at an international conference, where she will be formally presented with her Emerging Investigator Lectureship certificate. Details of her lectures will be announced in due course – keep an eye on the blog for details.

Read these articles by Elizabeth New:

A cobalt(II) complex with unique paraSHIFT responses to anion
E. S. O’Neill, J. L. Kolanowski, P. D. Bonnitcha and E. J. New
Chem. Commun., 2017, 53, 3571-3574
DOI: 10.1039/C7CC00619E, Communication

On the outside looking in: redefining the role of analytical chemistry in the biosciences
Dominic J. Hare and Elizabeth J. New
Chem. Commun., 2016, 52, 8918-8934
DOI: 10.1039/C6CC00128A, Feature Article
From themed collection 2016 Emerging Investigators

Fluorescent sensing of monofunctional platinum species
Clara Shen, Benjamin D. W. Harris, Lucy J. Dawson, Kellie A. Charles, Trevor W. Hambley and Elizabeth J. New
Chem. Commun., 2015, 51, 6312-6314
DOI: 10.1039/C4CC08077G, Communication,  Open Access

Imaging metals in biology: balancing sensitivity, selectivity and spatial resolution
Dominic J. Hare, Elizabeth J. New, Martin D. de Jonge and Gawain McColl
Chem. Soc. Rev., 2015, 44, 5941-5958
DOI: 10.1039/C5CS00055F, Tutorial Review,  Open Access

A FRET-based ratiometric redox probe for detecting oxidative stress by confocal microscopy, FLIM and flow cytometry
Amandeep Kaur, Mohammad A. Haghighatbin, Conor F. Hogan and Elizabeth J. New
Chem. Commun., 2015, 51, 10510-10513
DOI: 10.1039/C5CC03394B, Communication

The annual ChemComm Emerging Investigator Lectureship recognises emerging scientists in the early stages of their independent academic career. Nominations for the 2018 Emerging Investigator Lectureship will open later in the year – keep an eye on the blog for details, and read more about our previous winners.

2016:    Ang Li from the Shanghai Institute of Organic Chemistry, China

2015:    Deanne D’Alessandro from the University of Sydney, Australia

    Yong Sheng Zhao from the Beijing National Laboratory for Molecular Sciences, China

2014:    Xinliang Feng from the Max Planck Institute for Polymer Research, Germany

2014:    Tomislav Friščić from McGill University, Canada

2014:    Simon M. Humphrey from the University of Texas at Austin, USA

2013:    Louise A. Berben from the University of California at Davis, USA

2013:    Marina Kuimova from Imperial College London, UK

2012:    Hiromitsu Maeda from Ritsumeikan University, Japan

2011:    Scott Dalgarno from Heriot-Watt University, Edinburgh, UK

Also of interest: You can read the 2016 ChemComm Emerging Investigators Issue which highlights research from outstanding up-and-coming scientists and watch out for our 2017 Emerging Investigators issue – coming very soon. You can also take a look at our previous Emerging Investigator issues in 2011, 2012, 2013, 2014 and 2015.

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Commemorating Michael Faraday (1791-1867) – call for papers in physical chemistry

This year we are commemorating the 150th anniversary of the death of Michael Faraday, perhaps one of the most prolific and influential scientists who ever lived. His ground-breaking research into the relationship between electricity and magnetism ultimately led to the invention of the electric motor.

One of his most well-known creations, the Faraday cage, is the basis of MRI machines which are routinely used for a range of medical diagnoses. He also discovered benzene, pioneered research into nanotechnology, and gave his name to the Faraday Effect, Faraday’s Law, and the SI unit of capacitance, the farad.

At the Royal Society of Chemistry, we are honouring Michael Faraday with a special Chemical Communications web themed issue, highlighting key discoveries and developments in physical chemistry.

We encourage you to submit your best research to be included in this unique collection! More information about our article types can be found here. Submit at www.rsc.org/ChemComm by 31st July 2017! Please note that all submissions will be subject to peer review in accordance with the journal’s quality and standards. If you are interested in this opportunity, please email chemcomm-rsc@rsc.org

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Improving Sodium-Ion Batteries for Large-Scale Energy Storage

One of the greatest global challenges is the ever-growing demand for reliable, large-scale energy production.

The depletion of cost-effective fossil fuels and concerns about climate change are driving the need for clean energy sources derived from renewable technologies. Wind and solar power show significant potential as sustainable alternatives however, both solar photovoltaics and wind energy display intermittent output which has led to concerns regarding reliability for global energy production. As a result, there has been an increased demand for the development of large-scale energy storage.

Among energy storage technologies, lithium-ion batteries (LIBs) predominate however lithium’s high cost, abundance, unevenglobal distribution and safety concerns have limited its widespread application. In recent years, researchers have become interested in high energy sodium-ion batteries (SIBs) as a safer and less expensive alternative. Nevertheless, their inferior electrochemical performances, due to the larger size and heavier mass of sodium ions, has become a major hurdle in the development and implementation of SIBs.

In a recent ChemComm publication, Prof. Jun Chen of Nankai University has demonstrated the improved capabilities of SIBs using a manganite hydroxide (MnOOH)-based anode.

In the past, transition metal oxides, such as MnOx-based materials, have been used in LIBs as they possess a high theoretical capacity and—in some cases—improved conductivity. In this study by Chen and co-workers, MnOOH nanorods (figure, top) were synthesized, and were shown to display a higher initial Coulombic efficiency and rate performance compared to MnO2 (a common anode material in LIBs). Cyclic voltammetry (figure, bottom) and various other spectroscopic techniques were used to investigate the electrochemical properties and storage behaviour of MnOOH-SIBs. These experiments showed improvements in charge capacity and overall rate performance when compared to other transition metal oxides and sulfides.

The results of this work show promise toward the fabrication of high-performance SIBs which are encouraging alternatives for energy storage due to sustainable cost, improved thermal stability and transport safety. The performance of SIBs still lags behind that of LIBs but this study, among others, demonstrates that new electrode materials need to be explored in the development of SIBs and solving large-scale energy storage challenges.

To find out more see:

MnOOH nanorods as high-performance anodes for sodium ion batteries
Lianyi Shao, Qing Zhao and Jun Chen
DOI: 10.1039/C7CC00087A


Victoria Corless is currently completing her Ph.D. in organic chemistry with Prof. Andrei Yudin at The University of Toronto. Her research is centred on the synthesis of kinetically amphoteric molecules, which offer a versatile platform for the development of chemoselective transformations with particular emphasis on creating novel biologically active molecules.

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Soft drinks power origami cell

Graphical Abstract

Source: © Royal Society of Chemistry - The tiny fuel cell is made from a folded sheet of filter paper that holds the anode and cathode

Miniature fuel cell made from folded filter paper runs on sugary drinks.

Researchers in China have found a way to integrate the ancient Japanese art of paper folding, origami, into a miniature biofuel cell that can generate energy from soft drinks.

Biofuel cells use enzymes, instead of precious metals, as catalysts to oxidise their fuel. Miniature versions have excited researchers because they are portable and have high efficiency. They could provide power for implants or electronic contact lenses or harvest energy from perspiration. However, designing these small biofuel cells is difficult due to complicated assembly and high costs.


Read the full article in Chemistry World >>>


A miniature origami biofuel cell based on a consumed cathode
You Yu, Yujie Han, Baohua Lou, Lingling Zhang, Lei Hana and Shaojun Dong
Chem. Commun., 2016, 52, 13499-13502
DOI: 10.1039/C6CC07466A, Communication

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Cram Lehn Pedersen Prize 2017 – call for nominations

ISMSC-ISACS 2017, 2-6 July 2017, Cambridge, UK

The International Committee of the International Symposium on Macrocyclic and Supramolecular Chemistry is pleased to invite nominations for the Cram Lehn Pedersen Prize for young supramolecular chemists.

The Cram Lehn Pedersen Prize, named in honour of the winners of the 1987 Nobel Prize in Chemistry, recognises significant original and independent work in supramolecular chemistry.

Previous winners include Ivan Aprahamian, Feihe Huang, Oren Schermann, Tomoki Ogoshi, Jonathan Nitschke, and Amar Flood.

Those who are within 10 years of receiving their PhD on 31st December 2016 are eligible for the 2017 award. The winner will receive a prize of £2000 and free registration for the ISMSC-ISACS meeting in Cambridge, UK. In addition to giving a lecture at ISMSC-ISACS, a short lecture tour will be organised after the meeting in consultation with the Editor of Chemical Communications, the sponsor of the award.

Nomination Details:

You may nominate yourself or someone else. Please send your CV, list of publications (divided into publications from your PhD and post-doc, and those from your independent work), and if desired, a letter of support, or these materials for someone you wish to nominate, to Prof. Roger Harrison (ISMSC Secretary) at rgharris@chem.byu.edu by 31st December 2016.

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Professor Itaru Hamachi joins as Associate Editor

We are very pleased to welcome Professor Itaru Hamachi from Kyoto University as a new Associate Editor to the ChemComm team and look forward to working with him over the coming years.

Itaru is a chemical biologist with expertise in live-cell organic chemistry, chemical biology, bioorganic and bioinorganic chemistry, and supramolecular biomaterials. He is now accepting submissions to ChemComm in the area of chemical biology.

Itaru is looking froward to his new role:

I would like to encourage that new chemistry and chemical approaches between the chemistry and biology interfaces will appear in ChemComm, in order to decipher a lot of chemical-biology problems and also to create novel bio-inspired materials.

About Itaru:

Professor Itaru Hamachi was born in Fukuoka Prefecture, Japan in 1960 and received his Ph.D. in 1988 from Kyoto University under the guidance of the late Professor Iwao Tabushi. Immediately thereafter he joined Kyushu University, where he worked as an Assistant Professor for three years in the Kunitake laboratory before he became an Associate Professor in the Shinkai laboratory in 1992. In 2001, he became a Full Professor at IFOC, Kyushu University and moved to Kyoto University in 2005 where he currently heads the bioorganic chemistry wing.

Professor Hamachi has been a PRESTO investigator for 7 years (from 2000 to 2006) and a team leader of two CREST projects (from 2008 to 2013 and then from 2013 to 2018), which all are supported by the Japan Science and Technology (JST) Agency.

Submit your next top-notch, high-impact research now to Itaru Hamachi’s Editorial Office.



Itaru’s recent articles in ChemComm and other Royal Society of Chemistry journals include:*

Protein recognition using synthetic small-molecular binders toward optical protein sensing in vitro and in live cells
Ryou Kubota and Itaru Hamachi
Chem. Soc. Rev., 2015, 44, 4454-4471
DOI: 10.1039/C4CS00381K, Review Article

Ligand-directed dibromophenyl benzoate chemistry for rapid and selective acylation of intracellular natural proteins
Yousuke Takaoka, Yuki Nishikawa, Yuki Hashimoto, Kenta Sasaki and Itaru Hamachi
Chem. Sci., 2015, 6, 3217-3224
DOI: 10.1039/C5SC00190K, Edge Article
OA iconOpen Access

Hoechst tagging: a modular strategy to design synthetic fluorescent probes for live-cell nucleus imaging
Akinobu Nakamura, Kazumasa Takigawa, Yasutaka Kurishita, Keiko Kuwata, Manabu Ishida, Yasushi Shimoda, Itaru Hamachi and Shinya Tsukiji
Chem. Commun., 2014, 50, 6149-6152
DOI: 10.1039/C4CC01753F, Communication

*Access is free until 30/09/2016 through a registered RSC account.

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Ivan Aprahamian wins Cram Lehn Pedersen Prize

Photograph of Professor Ivan AprahamianThe International Committee of the International Symposium on Macrocyclic and Supramolecular Chemistry is delighted to announce that the 2016 Cram Lehn Pedersen Prize, given annually to an outstanding early-career supramolecular chemist, has been awarded to Professor Ivan Aprahamian, Dartmouth College, USA for his exciting research on molecular switches – congratulations!

As part of the Prize, Prof. Aprahamian will give a lecture at the 11th International Symposium on Macrocyclic and Supramolecular Chemistry meeting in Seoul, Korea which takes place from 10–14 July 2016.

Photograph of Dr Jeanne AndresDr Jeanne Andres (Deputy Editor of ChemComm) will be attending the event and will present the award in person. She would love to hear about your research and meet with our readers, authors and referees. Please do get in touch with Jeanne if you would like to arrange a meeting in advance.

We are also delighted to announce that the International Symposium on Macrocyclic and Supramolecular Chemistry in 2017 will be held in conjuction with ISACS: Challenges in Organic Materials & Supramolecular Chemistry.

Our keynote speakers will be:

  • François Diederich (ETH Zurich, Switzerland)
  • David Leigh (The University of Manchester, UK)
  • Jeffrey Long (University of California, Berkeley, USA)
  • Vivian Yam (University of Hong Kong, Hong Kong)
  • Xi Zhang (Tsinghua University, China)

Full details of all the confirmed speakers may be found on the event website.

We hope you can join us in Cambridge, UK – save the dates 2–6 July 2017!

While you are waiting you might like to check out some of our recent themed collections of articles in the area of supramolecular chemistry – Enjoy!

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Fluorescently finding a specific disease marker needle in a biological haystack

The early detection and monitoring of disease is a somewhat recent advancement in healthcare that offers the significant advantage of being able to treat an illness in its initial stages, rather than once it has already manifested itself in the patient. Such a feat requires, however, the ability to see very specific and characteristic disease markers in situ, not unlike the search for a needle in a haystack.
 
Luckily, with the advent of fluorescence (and other) imaging techniques, methods have been developed whereby, in combination with contrast agents that are able to interact with specific molecules in the body, cell chemistry and function can be observed with high sensitivity, and, more importantly, abnormalities in these processes noticed in real time.
 
The art and ultimate success of this fluorescence imaging comes from the design of the contrast agent employed – the probe should be able to selectively recognise and target the relevant disease marker reversibly and under biological conditions. A number of approaches currently exist that meet these requirements, one of which is the boronic acid recognition motif that is able to act as a molecular receptor for the 1,2- and 1,3-diols commonly expressed in carbohydrates and complex glycoproteins. Tony James and his team from the University of Bath, whose own research focuses on such use of boronic acid receptors in the detection of carbohydrates, have summarised the recent and exciting advances in this particular field of selective biological imaging.
 
The well-known and strong affinity of boronic acids for carbohydrates offers a convenient means of detecting commonly expressed markers in diseases including some cancers, as well as Alzheimer’s, autoimmune, and heart diseases. As such, the attachment of this relatively simple chemical moiety to fluorescent small molecular, polymeric or benzoxaborale-based probes offers a diagnostic tool that is able to detect, monitor, and aid in the personalised treatment of such significant and life-changing diseases.
 
This Feature Article convincingly highlights the impact that boronic acid-based fluorescence imaging will ultimately have on a range of important clinical and theranostic practices and their successes.
  
Read this hot ChemComm article in full:
X. Sun, W. Zhai, J. S. Fossey and T. D. James
Chem. Commun., 2016, 52, 3456–3469
DOI: 10.1039/C5CC08633G

About the Writer:
Anthea Blackburn is a guest Web Writer for Chemical Communications. Anthea hails from New Zealand, carried out her graduate studies in mechanostereochemistry under the guidance of Prof. Fraser Stoddart in the US, and has recently relocated to live in London. She is a recent addition to the Econic Technologies team, where she is working on the development of new catalysts for the environmentally beneficial preparation of polycarbonates from CO2.
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Nominate now for the 2016 Cram Lehn Pedersen Prize in Supramolecular Chemistry

The International Committee of the International Symposium on Macrocyclic and Supramolecular Chemistry is pleased to invite nominations for the Cram Lehn Pedersen Prize for young supramolecular chemists.

The Cram Lehn Pedersen Prize, named in honour of the winners of the 1987 Nobel Prize in Chemistry, recognises significant original and independent work in supramolecular chemistry.

Previous winners include Feihe Huang, Oren Schermann, Tomoki Ogoshi, Jonathan Nitschke, and Amar Flood.

Those who are within 10 years of receiving their PhD on 31st December 2015 are eligible for the 2016 award. The winner will receive a prize of £2000 and free registration for the ISMSC meeting in Seoul, Korea. In addition to giving a lecture at ISMSC, a short lecture tour will be organised after the meeting in consultation with the Editor of Chemical Communications, the sponsor of the award.

Nomination Details:

You may nominate yourself or someone else. Please send your CV, list of publications (divided into publications from your PhD and post-doc, and those from your independent work), and if desired, a letter of support, or these materials for someone you wish to nominate, to Prof. Roger Harrison (ISMSC Secretary) at rgharris@chem.byu.edu by 31st January 2016.

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