Author Archive

Ginkgo biloba extract used to make Tamiflu

Graphical abstract: Extraction and isolation of shikimic acid from Ginkgo biloba leaves utilizing an ionic liquid that dissolves celluloseA new way of obtaining shikimic acid, the compound needed to make Tamiflu, has been discovered. Shikimic acid is normally obtained from star anise, a Chinese cooking spice. The shortage of star anise caused Roche problems a few years ago, when the demand for Tamiflu peaked during the H1N1 pandemic in 2009, so new sources are constantly being sought.

Toyonobu Usuki, from Sophia University, Tokyo, found that shikimic acid could be isolated from ginkgo biloba leaves using an ionic liquid. Ginkgo biloba is a tree mainly found in China and has often been used in Chinese medicine.

Find out more – read Usuki’s ChemComm communication.

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Two for one – cleaning water and generating energy

nanotube arrayA fuel cell system that can generate electricity from organic compounds and clean up wastewater at the same time has been developed by scientists in China.

Yanbiao Liu from Shanghai Jiao Tong University and colleagues made a photocatalytic fuel cell comprising a TiO2-nanotube-array (TNA) anode and a platinum-based cathode. The cell uses light energy to degrade organic compounds in wastewater, generating electrons that pass through to the cathode, which converts the chemical energy into electrical energy.

Interested in learning more? Read the full news story in Chemistry World and download the team’s ChemComm communication.

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Sugar injection to beat hospital infection

BacteriaA carbohydrate from the surface of the most virulent strain of the bacterium Clostridium difficile has been synthesised by chemists in Germany. The molecule could be used to develop a vaccine against the infection.

C. difficile infections are the most common cause of hospital acquired diarrhoea and can lead to the death of elderly patients and those with weakened immune systems.’C. difficile is on the rise in industrialised countries,’ says Peter Seeberger, who led the team that carried out the research at the Max Planck Institute of Colloids and Interfaces, Potsdam. ‘There is a need for a vaccine but it’s a big challenge.’

Find out more about Seeberger’s progress towards developing a vaccine in the full Chemistry World news story and download his ChemComm communication, free for a limited period.

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Artificial Photosynthesis – submission deadline extended

Due to popular demand, the submission deadline for ChemComm‘s Artificial Photosynthesis web theme has been extended until 30th September 2011.

Visit the original announcement for more details about the issue.

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ISMSC: Cram Lehn Pedersen Prize awarded

Professor Amar Flood delivered the inaugural Cram Lehn Pedersen Prize lecture at at the 6th International Symposium on Macrocyclic and Supramolecular Chemistry (6-ISMSC) in Brighton last week. The lecture, entitled ‘Binding and releasing anions with CH hydrogen-bonded receptors’, discussed his group’s efforts to regulate chloride concentrations in solution using aryl-triazole foldamers bearing azobenzene units. The foldamers can reversibly bind and liberate chloride depending on the wavelength of light shone on them.
The prize was sponsored by ChemComm and Dr Robert Eagling, ChemComm Editor, presented the certificate to Professor Flood. 
Professor Amar Flood (right) receives his award certificate from ChemComm Editor Dr Robert Eagling

You can read some of Professor Flood’s recent research in the recent supramolecular chemistry web theme issue:
Two levels of conformational pre-organization consolidate strong CH hydrogen bonds in chloride–triazolophane complexes
Yuran Hua, Raghunath O. Ramabhadran, Jonathan A. Karty, Krishnan Raghavachari and Amar H. Flood, Chem. Commun., 2011, 47, 5979-5981

Find out more about ISMSC in my conference blog.

And don’t forget – there is still time to submit your nomination for the 2012 Cram Lehn Pedersen prize. Deadline 31st July 2011. See the call for nominations for more details.

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Organocatalysis – announcing a joint ChemComm–OBC web theme

We are delighted to announce a forthcoming ChemCommOrganic & Biomolecular Chemistry (OBC) web themed issue:

Organocatalysis

Guest editors: Keiji Maruoka (Kyoto University), Hisashi Yamamoto (University of Chicago), Liu-Zhu Gong (University of Science and Technology of China) and Benjamin List (Max-Planck-Institut für Kohlenforschung)

Submission deadline: 29th February 2012

We are now inviting submissions for this web theme, which will be a celebration of current achievements and future perspectives in this exciting field of research.

ChemComm and OBC are both welcoming urgent communications; OBC also welcomes full papers. Please feel free to submit to either or both journals.

All manuscripts will undergo strict peer review and should be very important and conceptually significant in accord with the ChemComm and OBC mandates

Publication of the peer-reviewed articles will occur without delay to ensure the timely dissemination of the work. The articles will then be assembled on the RSC Publishing Platform as a web-based thematic issue, to permit readers to consult and download individual contributions from the entire series.

Communications for this web theme can be submitted anytime from now until 29th February using ChemComm‘s and OBC‘s web submission system. Please add the phrase ‘organocatalysis web theme‘ in the comments to the editor field.

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Tetrafluorocyclohexane: a novel polar motif

The cyclohexane motif is among the most common in organic chemistry but selectively fluorinated versions are rare. The high polarity of C–F bonds can influence the conformation and reactivity of molecules, making fluorinated molecules high on the target list of many chemists, including David O’Hagan at the University of St Andrews, UK.

His team have managed to make 1,2,3,4-tetrafluorocyclohexane, the first example of a cyclohexane with more than two vicinal fluorine atoms. The all syn stereochemistry forces two of the C–F bonds into 1,3-diaxial orientations. This diaxial interaction makes the molecule polar, which O’Hagan suggests could make it a novel polar structural motif for organic materials.

Graphical abstract: Synthesis and structure of all-syn-1,2,3,4-tetrafluorocyclohexane

Find out more: download O’Hagan’s ChemComm communication for free until 28th July.

Also of interest: Fluorine chemistry web theme

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Quantum dots selectively label endoplasmic reticulum

Graphical abstract: Selective labeling of the endoplasmic reticulum in live cells with silicon quantum dotsScientists are a step closer to understanding how an important cell organelle works, which could lead to new insight into disease such as diabetes and Alzheimer’s disease.

The endoplasmic reticulum (ER) plays a critical role in protein synthesis and transport. Its malfunction can lead to serious diseases so it is important to be able to observe how it works. 

Yukio Yamaguchi and colleagues at the University of Tokyo, Japan, have managed to selectively label the ER in live cells using quantum dots (QDs). Although organic dyes have previously been used for this purpose, Yamaguchi’s QDs are less toxic and more photostable. 

The QDs’ photoluminescence enabled the team to view the ER using a confocal microscope, making them a powerful tool for long-term real-time observation of the ER, Yamaguchi says.

Find out more by downloading the communication.

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Metal organic frameworks for hydrogen storage

Hydrogen is seen by many as the energy to fuel the future of the automotive industry. But its low polluting profile and high energy efficiency are currently overshadowed by the technical difficulties in developing safe and efficient storage strategies for mobile applications.

Alternatives to the common high pressure tanks have been looked for over the years and some promising results came from the use of metal hydrides, formic acid, carbon nanotubes, metal organic frameworks (MOFs) as storage supports.

MOF research for hydrogen storage is a young field, established in the early 2000s when reports of the application of these porous materials started to appear in journals such as Science (Science, 2003, 300 (5622), 1127-1129 DOI: 10.1126/science.1083440). After the first proofs of concept, research has moved on increasing the hydrogen absorption capabilities of these materials by screening different metals, organic linkers and fabrication techniques.

The group lead by Champness and Schröder at the University of Nottingham, not new to the field (Angew. Chem. Int. Ed. 2006, 45, 7358 –7364, DOI: 10.1002/anie.200601991; Nature Chemistry 1, 487 – 493 (2009), DOI:10.1038/nchem.333), has recently focused on the development of two new scandium(III)-based MOFs that exhibit promising hydrogen absorption qualities. The novel materials, based on the general formula [M22-OH)(OCR)4)], were characterised and their performance as storage supports tested.

Graphical abstract: Highly porous and robust scandium-based metal–organic frameworks for hydrogen storageThe novel MOFs, NOTT-400 and NOTT-401, share the same metal-based fragment as building block and differ from each other by the organic linker employed (H4BPTC and H2TDA). They retained high crystallinity up to 500 °C and 350 °C respectively and were successfully reacted with acetone and degassed to afford the fully desolvated material ready for use.

The hydrogen absorption capabilities were tested at 77 and 87 K at hydrogen pressures ranging up to 20 bar with a maximum absorption of 4.44 wt% at 20 bar for NOTT-401. The absorption kinetics showed a very fast intake, reaching equilibrium in about 3 minutes, and good reversibility. No hysteresis was observed.

For the original communication see:
Highly porous and robust scandium-based metal–organic frameworks for hydrogen storage
Ilich A. Ibarra, Sihai Yang, Xiang Lin, Alexander J. Blake, Pierre J. Rizkallah, Harriott Nowell, David R. Allan, Neil R. Champness, Peter Hubberstey and Martin Schröder
Chem. Commun., 2011, DOI: 10.1039/C1CC11168J

Posted on behalf of Dr. Giorgio De Faveri, Web Writer for Catalysis Science & Technology.

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Magnetic nanoparticles detect low levels of cyanide

Chinese scientists have reported dumbbell-shaped nanoparticles capable of detecting cyanide concentrations as low as 4 x 10-7 M in drinking water. This low detection limit, which is below the acceptable limit advised by the World Health Organization, is attributed to a combination of fluorescence detection with a filtering process called ‘magnetic concentration-washing’.

The toxicity of cyanide and its potential prevalence in drinking water has made easy detection of cyanide an active area of research. Gold nanoparticles have attracted attention as cyanide sensors due to their selectivity for cyanide over other anions. Now, Shaojun Dong and colleagues at the Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, have adapted a bifunctional nanoparticle made up of Au and magnetic Fe3O4 nanoparticles for sensitive detection of cyanide, even in the presence of interfering species. 

Schematic depiction of the turn-on fluorescent detection of cyanide based on the dual-functional Au–Fe3O4 dumbbell nanoparticles.

The group detected cyanide by relying on what is known as the ‘inner filter effect’, observed when two molecules present in a solution have overlapping absorption and emission wavelengths. The fluorescence emission from a fluorophore is blocked, or reabsorbed, by the second molecule, reducing or even quenching the overall fluorescence of the solution. In the present system, the excitation and emission energy for the fluorophore Rhodamine B is quenched by the Au-Fe3O4 nanoparticles. However, addition of cyanide to the sample reduces the gold component of the nanoparticles by forming an Au(CN)2 complex. This change in the structure alters the nanoparticles’ absorbance spectra and the Rhodamine B emissions are no longer fully absorbed. The team calculated the amount of cyanide present in a sample by monitoring the change in fluorescence.

To extend this detection method for use with environmental samples, which may contain dyes or other contaminants that absorb or emit at a similar wavelength to Rhodamine B, Dong and colleagues implemented a ‘magnetic concentration-washing process’. In it, the Au-Fe3O4 nanoparticles are magnetically separated from the sample solution after they have reacted with any cyanide present in the sample. This magnetic separation retains the bifunctional nanoparticles and leaves any interfering species behind. Pure buffered water containing additional Rhodamine B is added and the fluorescence is monitored. The authors showed that two cycles of this process were enough to remove any interfering species and accurately detect cyanide levels. 

To find out more, read the full article:

Dual-Functonal Au-Fe3O4 Dumbbell Nanoparticles for Sensitive and Selective Turn-on Fluorescent Detection of Cyanide Based on the Inner Filter Effect
Yueming Zhai, Lihua Jin, Ping Wang and Shaojun Dong, Chem. Commun., 2011, DOI: 10.1039/C1CC13149D 

Posted on behalf of Patricia Pantoș, web writer for ChemComm.

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