Natural products go with the flow

Technology that could bring flow chemistry into the domain of complex natural product synthesis has been developed by UK scientists. 

The best things in life don’t come without a struggle – or so the saying goes. It certainly appears that way with chemistry. Very rarely are the chemicals desirable in a modern society made in a single step. Indeed, it is not unusual for a drug to require at least 10 distinct processes. Conventional batch synthesis can often put a considerable burden on the efficiency of these steps, demanding excess chemicals and solvents and generating large and unacceptable quantities of waste materials. 

Now, a team led by Steven Ley at the University of Cambridge are advocating a more machine-assisted approach, particularly using flow chemistry techniques combined with scavenger materials to bring about multi-step operations with in-line purification. 

Natural products go with the flow

To find out more, read the full news story in Chemistry World and download Ley’s Edge article for free from Chemical Science.

Also of interest:
Unclogging the problems of flow chemistry: US scientists have found a way to stop solid by-products clogging channels in continuous flow reactors

 

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Who’s who in Chemical Science

We have 17 world-leading Associate Editors working with Editor-in-Chief David MacMillan to ensure that Chemical Science represents the new thinking from across the chemical sciences. But can you match the faces with the names? Number 1, David MacMillan, is N – but what about the others?

Post your answers below – all correct answers will be in with the chance of winning a prize …

1. David MacMillan, Princeton University, USA
Editor-in-Chief
2. Chris Bielawski, University of Texas, Austin
Associate Editor: Polymer Science
3. Stephen L Buchwald, MIT, USA
Associate Editor: Organic Chemistry
4. Thomas Carell, Ludwig-Maximilians-Universität München, Germany
Associate Editor: Chemical Biology and Bioorganic Chemistry
5. Benjamin F Cravatt, Scripps, USA
Associate Editor: Chemical Biology
6. Christopher C Cummins, MIT, USA
Associate Editor: Inorganic and Organometallic Chemistry
7. Kazunari Domen, University of Tokyo, Japan
Associate Editor: Physical Chemistry, Energy and Surface Science
8. Matthew Gaunt, University of Cambridge, UK
Associate Editor: Organic Chemistry
9. Hubert Girault, Ecole Polytechnique Fédérale de Lausanne, Switzerland
Associate Editor: Analytical Science
10. David A Leigh, University of Edinburgh, UK
Associate Editor: Supramolecular Chemistry
11. Kopin Liu, Academia Sinica, Taiwan
Associate Editor: Physical Chemistry
12. Jeffrey R Long, UC Berkeley, USA
Associate Editor: Inorganic Chemistry
13. Wonwoo Nam, Ewha Womans University, Korea
Associate Editor: Bioinorganic Chemistry
14. Colin Nuckolls, Columbia University, USA
Associate Editor: Organic Materials
15. Teri Odom, Northwestern University, USA
Associate Editor: Nanoscience
16. Matthew J Rosseinsky, University of Liverpool, UK
Associate Editor: Inorganic Materials
17. F Dean Toste UC Berkeley, USA
Associate Editor: Organic Chemistry
18. Haw Yang, Princeton University, USA
Associate Editor: Physical Chemistry

Five prize-winners will be selected at random from winning entrants who have supplied a valid email address with their correct entry. Competition closes at 24.00 GMT on 30th April 2011. Winners will be notified by email.

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Probing Alzheimer’s disease with transition metals

amyloid fibrils

Group 9 metal complexes can inhibit amyloid aggregation, thought to be responsible for neurodegeneration in Alzheimer’s disease patients.

Dik-Lung Ma (University of Hong Kong) and colleagues made iridium(III) and rhodium(III) complexes that can both inhibit the aggregation of Ab1-40 peptides and acts as luminescent probes for the peptides. Their iridium complex is the first example of a transition metal complex that displays a ‘switch-on’ luminescence response upon binding to Ab1-40 peptides; the magnitude of response can be used to distinguish between the peptide’s monomeric and fibrillar forms.

Read the full Edge Article for free in Chemical Science.

Submit your exceptional research today to be seen with the best.

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Do catalytic reactions take place inside MOF pores?

Scientists have made a large-pored metal-organic framework (MOF) that they say provides a conclusive answer to a long standing issue: do catalytic reactions take place inside the pores?

Chiral MOFs are of great interest for enantioselective catalysis but they have had limited success as enantioselective catalysis in terms of catalytic turnover and stereoselectivity, partly due to their lack of void space. There are a number of reports of chiral MOFs with pores large enough to accommodate whole molecules. It has been assumed that the reactions occur both at the surface and also in the pores but until now the evidence has been circumstantial, according to Nakcheol Jeong at Korea University in Seoul.

Jeong’s MOF has organic linkers that maintain local chirality with functional groups that can be modified on demand to produce new catalysts. He used the MOF catalyst for a carbonyl-ene reaction and says he has conclusively proved that the reaction occurs entirely inside the pores.

You can read Jeong’s Edge article for free in Chemical Science.  Let us know if you agree with the conclusions by leaving your comments below.

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Christopher Bielawski appointed Chemical Science Associate Editor

New Associate Editor for polymer science

I am pleased to announce that Professor Christopher Bielawski (University of Texas at Austin, USA) has joined the Chemical Science Editorial Board as Associate Editor for polymer science.

Professor Bielawski’s research program lies at the interface of polymer science and materials chemistry, and focuses on the synthesis and study of unique organic and organometallic macromolecules.

His Chemical Science Editorial Office opens for submissions on 1st March 2011. We look forward to working with him and welcome him to his new role.

Also of interest:
A benzocrown-6-calix[4]arene methacrylate copolymer: Selective extraction of caesium ions from a multi-component system
Brett M. Rambo, Sung Kuk Kim, Jong Seung Kim, Christopher W. Bielawski and Jonathan L. Sessler
Chem. Sci., 2010, 1, 716-722

Synthesis and self-assembly of poly(3-hexylthiophene)-block-poly(acrylic acid)
Zicheng Li, Robert J. Ono, Zong-Quan Wu and Christopher W. Bielawski
Chem. Commun., 2011, 47, 197-199

The chemistry of graphene oxide
Daniel R. Dreyer, Sungjin Park, Christopher W. Bielawski and Rodney S. Ruoff
Chem. Soc. Rev., 2010, 39, 228-240

Rachel O’Reilly joins the Chem Soc Rev Editorial Board

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Phosphorus radicals stabilised by carbenes

Singlet carbenes can be used to isolate elusive neutral phosphorus radicals in the solid state, researchers have discovered. 

Very few phosphorus radicals have been isolated and characterised in the solid state because they tend to dimerise. Now, Guy Bertrand and colleagues have reported two phosphorus radicals, one stabilised by a transition metal and the other stabilised by N-heterocyclic carbenes (NHCs), which allowed them to compare the electronic effects of both substituents. While the transition metal was better at delocalising the spin density from the phosphorus nucleus, NHCs are sufficiently stabilising to allow isolation and characterisation of the neutral radical.

Download Bertrand’s Edge article from Chemical Science to read more.

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Speed dating for pharmaceuticals

A simple analysis of hydrogen bond strengths finds the best crystallisation partners for drugs, say UK scientists.

The properties of active pharmaceuticals can be altered by crystallising them with an inactive partner molecule in a cocrystal. Finding good cocrystal partners experimentally is time consuming, and current computational methods are laborious as they calculate the crystal structure, atom by atom. Cocrystals could provide new ways to deliver drugs and improve their properties, so the search for them is on.

Hydrogen bonds and other electrostatic interactions influence how molecules interact, and the energies of such gaseous interactions are straightforward to calculate. Chris Hunter and colleagues at the University of Sheffield, UK, University of Barcelona, Spain, and AstraZeneca, UK, assumed that these interactions don’t change in a solid crystal and that the crystal packing is less important than electrostatics. These are controversial assumptions but the calculations based on them work.

Hydrogen bonding

Find out more in Chemistry World and download the full Chemical Science Edge article for free.

Also of interest:
The role of functional group concentration in solvation thermodynamics
Niklaas J. Buurma, Joanne L. Cook, Christopher A. Hunter, Caroline M. R. Low and Jeremy G. Vinter,  Chem. Sci., 2010, 1, 242-246

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Chemical Science Editors among top 100 chemists

David MacMillan, Stephen Buchwald, Dean Toste and Jeffrey Long have recently been identified as some of the world’s top 100 chemists. That’s great news for them and also great news for Chemical Science – we’re delighted to have so many world leaders handling manuscripts and setting the scientific standards for our flagship journal.

The top 100 list, compiled by Thomson Reuters, also contains a number of Chemical Science authors. Overall, this is an impressive position for such a new journal, putting us on a par with other more established premier journals in the general chemistry arena. So if you want your paper to be seen and handled by the best, submit to Chemical Science.

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Building up a natural product toolkit

US scientists have come up with a method that makes it easier to extract compounds that are difficult to isolate from crude natural product mixtures.

Erin Carlson and her team at the University of Indiana, Bloomington, used resins to target and isolate desired compounds in crude extract mixtures, in this case alcohols.

Isolating compounds from natural product mixtures is important because of their high propensity to interact with biological targets. Nearly half of currently available drugs are from natural products and pharmaceutical companies analyse crude extracts from, for example, plant materials for biological activity. Any active compounds are purified either by extraction and/or chromatography.

Current extraction methods rely on the compounds’ physical properties such as solubility, polarity or size. Despite advances in separation technology, purification is still problematic and time-consuming. ‘Isolation of trace quantities of new natural products is often thwarted by the crude extract containing a plethora of compounds, with a heavy reliance on multiple liquid chromatography processes,’ says Gordon Florence, an expert in bioactive natural products from the University of St Andrews, UK.

Carlson’s team used a silyl-functionalised resin to capture and bind to the alcohol anisomycin – a protein biosynthesis inhibitor – from a mixture of compounds extracted from soil bacteria Streptomyces griseolus. The team washed the resin to remove non-targeted compounds before cleaving the anisomycin from the resin and found that the resin didn’t bind to compounds with functional groups other than alcohol. Following regeneration, the resin could be reused.


A silyl-functionalised resin was used to capture and bind to the alcohol anisomycin – a protein biosynthesis inhibitor – from a mixture of compounds extracted from soil bacteria Streptomyces griseolus

Read the full Chemistry World article here

Link to journal Article
Chemoselective enrichment for natural products discovery
Antoinette Y. Odendaal, Darci J. Trader and Erin E. Carlson,
Chem. Sci., 2011, DOI: 10.1039/c0sc00620c

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Award winning Editor-in-Chief

Many congratulations to Professor David MacMillan from the Chemical Science team, who has won the ACS award for creative work in Synthetic Organic Chemistry.

We are delighted to learn that Professor MacMillan, Editor-in-Chief for the Royal Society of Chemistry’s new flagship journal Chemical Science, has been recognised for his contributions to organic chemistry, especially for his ground breaking research in organocatalysis.  

Professor MacMillan sporting a Chemical Science hat at the Pacifichem meeting back in December (2010)

 

Professor MacMillan has published a couple of Edge Articles in Chemical Science, which are freely available for you to download:-

 

Professor MacMillan will receive his prize at the 241st ACS national meeting in Anaheim, CA, in the spring. Dr Robert Eagling, Chemical Science Managing Editor, will also be attending this meeting and if you would like to arrange a meeting with Robert, then please contact the Chemical Science Editorial Office. 

 

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