Organic: Potential new anthrax vaccine

Scientists in France and Germany have shown that a simplified version of an anthrax polysaccharide can be used as a potential vaccine against Bacillus anthracis. The disaccharide analogue of the anthrax tetrasaccharide is conjugated to bovine serum albumin, with the aim to obtain an antigen able to induce specific antibodies.

Potential new anthrax vaccine

Link to journal article:
Organic: Potential new anthrax vaccine
Cyrille Grandjean, Ophélie Milhomme, Suzanne M Köhler, David Ropartz, David Lesur, Serge Pilard, Florence Djedaïni-Pilard and Wolfgang Beyer
Org. Biomol. Chem., Accepted Manuscript, 2012
DOI: 10.1039/c2ob26131f

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OBC issue 38 online now: Kulinkovich cyclopropanation, organozinc halides and much, much more

An overview of what is in this week’s issue of OBC

OBC issue 38 front coverFeaturing on this week’s front cover is a review from Margaret A. Brimble summarising the application of the Kulinkovich cyclopropanation in the transformation of esters with diisopropoxytitanacyclopropane derivatives into cyclopropanols in the total synthesis of natural biologically active compounds.

The Kulinkovich hydroxycyclopropanation reaction in natural product synthesis
Isabell Haym and Margaret A. Brimble

OBC issue 38 inside coverOn the inside cover is a HOT communication from Ying Fu et al. presenting a general procedure for the nucleophilic addition of organozinc halides to nitrones using trimethylsilyl chloride as a promoter and as a good protection reagent for the sensitive N-hydroxylamine group.

Trimethylsilyl chloride promoted synthesis of α-branched amines by nucleophilic addition of organozinc halides to nitrones
Ying Fu, Yanhua Liu, Yaojuan Chen, Helmut M. Hügel, Minzhu Wang, Danfeng Huang and Yulai Hu

Both articles are free to access for 6 weeks

Also in this issue:

3 more HOT articles:

Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis
David J. Burns, Shuji Hachisu, Peter O’Brien and Richard J. K. Taylor
DOI: 10.1039/C2OB26406D

An alternative one-pot gold-catalyzed approach to the assembly of 11H-indolo[3,2-c]quinolines
Giorgio Abbiati, Antonio Arcadi, Marco Chiarini, Fabio Marinelli, Emanuela Pietropaolo and Elisabetta Rossi
DOI: 10.1039/C2OB26380G

Steric effects on the catalytic activities of zinc(II) complexes containing [12]aneN3 ligating units in the cleavage of the RNA and DNA model phosphates
Yang Song, Ju Zan, Hao Yan, Zhong-Lin Lu and Ruibing Wang
DOI: 10.1039/C2OB25624J

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Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis

This article is HOT as recommended by the referees, and is free to access for 4 weeks.

In this Communication Peter O’Brien and colleagues from the University of York describe a short and efficient asymmetric synthesis of a chiral cyclohexenone derivative ((4S,5S)-dihydroxycyclohexen-1-one ). This derivative is a very useful synthon for a variety of natural products, as shown by O’Brien et al., who prepare 2 cyclohexenone natural products isolated from the mycelia of Lasiodiplodia theobromae.

The approach presented has been described as being ‘elegant chemistry which uses symmetry breaking reactions to quickly reach a synthetic goal.’

Find out more by downloading the Communication now….

Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis
David J. Burns, Shuji Hachisu, Peter O’Brien and Richard J. K. Taylor
DOI: 10.1039/C2OB26406D

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An alternative one-pot gold-catalyzed approach to the assembly of 11H-indolo[3,2-c]quinolines

This article is HOT as recommended by the referees.

In this HOT paper Antonio Arcadi, Università degli Studi di L’Aquila, and colleagues present a newly developed one-pot gold-catalysed approach to the assembly of 11H-indolo[3,2-c]quinolines from readily available unprotected 2-[2-(2-aminophenyl)ethynyl]anilines and aldehydes.

Arcadi et al. use the clever idea of first using a fast regio-selective intramolecular reaction, followed by a slower intermolecular condensation and subsequent cyclisation and final hydrogen transfer nicely provides a fast, synthetically efficient and elegant access to indolo[3,2-c]quinolines. With its broad scope, mild conditions and high regioselectivity this could be a valuable alternative to protocols previously described in the literature.

Find out more by downloading this paper today. It’s free to access for 4 weeks so grab it whilst you can.

An alternative one-pot gold-catalyzed approach to the assembly of 11H-indolo[3,2-c]quinolines
Giorgio Abbiati, Antonio Arcadi, Marco Chiarini, Fabio Marinelli, Emanuela Pietropaolo and Elisabetta Rossi
DOI: 10.1039/C2OB26380G

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Steric effects on the catalytic activities of zinc(II) complexes in the cleavage of the RNA and DNA model phosphates

This article is HOT as recommended by the referees.

This manuscript from Zhong-Lin Lu and co-workers presents the preparation of a series of mononuclear and dinuclear zinc(II) complexes with ligands bearing different numbers of N-methyl groups, and includes a thorough kinetic study towards the hydrolytic cleavage of RNA and DNA model substrates.

The study focuses on the influence of steric effects on the catalytic efficiency and for the first time probes the effect of N-methylation of triazacyclododecane ligands. The N-methylation substantially reduces the co-operative behaviour between mononuclear zinc complexes and for the dinuclear complexes the activities are also substantially reduced but are still faster than the background reaction without the metal-complex.

Find out more by clicking below… download it now, it’s free for 4 weeks!

Steric effects on the catalytic activities of zinc(II) complexes containing [12]aneN3 ligating units in the cleavage of the RNA and DNA model phosphates
Yang Song, Ju Zan, Hao Yan, Zhong-Lin Lu and Ruibing Wang
DOI: 10.1039/C2OB25624J

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Chemical biology and medicinal: Potential agents to treat Alzheimer’s disease

Scientists in Germany have worked on optimising compounds that reduce the formation of amyloid β-peptides, which play a crucial role in the development and progression of Alzheimer’s disease. The team varied the membrane anchor, spacer and pharmacophore building blocks on BACE1 inhibitors to make tripartite structures (assembled by covalent coupling of BACE1 inhibitors with membrane anchors via suitable spacers).

Several BACE1 inhibitors have already been reported, but here, the team has shown that the cellular activity of small-molecule BACE1 inhibitors can be significantly increased by membrane targeting via a spacer with a raftophilic membrane anchor.

Optimisation of BACE1 Inhibition of Tripartite Structures by Modification of Membrane Anchor, Spacer and Pharmacophore – Development of Potential Agents for the Treatment of Alzheimer’s Disease
Hans-Joachim Knölker
DOI: 10.1039/C2OB26103K

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Physical organic chemistry: An article collection

A free collection of high impact articles on physical organic chemistry from the RSC’s ChemComm, Chemical Science and Organic & Biomolecular Chemistry (OBC).

Physical organic chemistry, the study of the underlying principles and rationale of organic reactions which looks at the interrelationships between the structure and reactivity of organic molecules, now encompasses a wider range of contexts than ever before.

Making use of tools such as chemical kinetics, quantum chemistry, thermochemistry, chemical equilibrium and computational chemistry, to name but a few, researchers are investigating topics such as:

•    Supramolecular interactions, aggregation and reactivity
•    The computation of transition states and mechanisms
•    Molecular recognition, reactions and catalysis in biology
•    Materials where molecular structure controls function
•    Structure activity correlations
•    Mechanisms in synthesis and catalysis

To highlight some of the cutting edge research that ChemComm, Chemical Science and Organic & Biomolecular Chemistry receive we have collected a selection of articles for you to enjoy. These will be free to access until 25th September!

Click here for the full list of free articles

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Using Chemistry to improve Agricultural Productivity

Chemistry for Tomorrow’s World 2012: Using Chemistry to Improve Agricultural Productivity

6 pm, 26 September 2012
Chemistry Centre, Burlington House, London

Join us at the RSC’s Chemistry Centre in London to hear about how synthetic organic chemistry can help to feed the world.

Azoxystrobin is the world’s leading agricultural fungicide. It is a fully synthetic compound, whose invention was inspired by the structure and activity of the naturally-occurring fungicide strobilurin A. Today it is used worldwide to control fungi growing on over 120 types of crop, improving plant health, raising quality and increasing yield. The success of the project highlights the crucial importance of chemistry in meeting grand challenges such as global food security and the broader applicability of skills such as natural product synthesis. Our keynote speaker Dr John Clough led the team of chemists at Syngenta that invented azoxystrobin. He will discuss the key role that synthetic organic chemistry played in creating an effective and safe fungicide.

This event will be held in the Chemistry Centre on 26 September at the RSC’s recently refurbished building in Burlington House, London. Doors will open at 17:30 for refreshments. The event will begin at 18:00 and will finish with a wine reception. Please follow the link here for information and to register for the event.

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Stimulate your senses with OBC issue 37

OBC issue 37 has arrived, hot off the press, so why not put your feet up and have a cup of coffee as you browse through its contents. Prefer decaf? Well the work on this week’s front cover might be able to help you find out if that coffee you have really is decaffeinated…

…. Kay Severin and colleagues from École Polytechnique Fédérale de Lausanne (EPFL) have synthesised a dye (3,4:3’,4’-bibenzo[b]thiophene-2,2’-disulfonate) that can be used as a sensitive and selective molecular probe for the fluorimetric detection of caffeine in water with a better sensitivity and selectivity than previously reported caffeine sensors.

A ratiometric fluorescence sensor for caffeine
Nicolas Luisier, Albert Ruggi, Stephan N. Steinmann, Laurane Favre, Nicolas Gaeng, Clémence Corminboeuf and Kay Severin

On the inside cover is a communication from P. Venkatesu et al. demonstrating the ability of water and a protic ionic liquid, triethyl ammonium phosphate (TEAP) to act as refolding additives for the urea-induced chemical denaturated state of the two enzymes, α-chymotrypsin and succinylated Con A. Water and TEAP are shown to efficient and effective additives, with the enzymatic activity of the enzymes’ being regained and in some cases even enhanced.

Water and a protic ionic liquid acted as refolding additives for chemically denatured enzymes
Pankaj Attri, P. Venkatesu and Anil Kumar

Both articles can be downloaded free for the next 6 weeks, and they are just a click away….

Go to the issue….

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Organometallics in catalysis: an article collection

A collection of high impact articles focusing on organometallic complexes in catalysis, from the RSC’s Catalysis Science & Technology, ChemComm, Chemical Science, Dalton Transactions, Organic & Biomolecular Chemistry (OBC) and RSC Advances

Perhaps the most well-known applications of organometallics in catalysis are the Ziegler–Natta catalysts which are used to generate polymers, the catalysts are made up of mixtures of transition metal halides and organo-aluminium complexes. Karl Ziegler and Giulio Natta were awarded the 1963 Nobel Prize in Chemistry for their discovery and development of the catalysts, which today are the most commonly used for the manufacture of polythene.

The esteemed history of organometallics are not to be under-estimated and include Grignard’s reagents, the Heck reaction, Schrock catalysts, Grubbs’ catalysts and the Suzuki Coupling to name just a few. Organometallic compounds have revolutionised science and industry and to keep you up to date with the latest break-through research being made across all areas of organometallics in catalysis, we have made this cross-journal article collection free until the 26th September.

Click here for the full list of free articles

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