Organic & Biomolecular Chemistry Blog

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

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Go to the issue….

Issue 35 of Organic & Biomolecular Chemistry is now available online for you to access today!

On the front cover this weeks is the work of Chi-Ming Che and colleagues from The University of Hong Kong, who present a gold(I)/chiral Brønsted acid cooperative catalytic system for the efficient one-pot asymmetric synthesis of tetrahydroquinolines, with one or two chiral centres at different positions as well as highly divergent functional groups, from reaction of 2-aminobenzaldehydes or 2-aminophenones with alkynes.

Highly regio-, diastereo- and enantioselective one-pot gold/chiral Brønsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines
Xin-Yuan Liu, Ya-Ping Xiao, Fung-Ming Siu, Li-Chen Ni, Yong Chen, Lin Wang and Chi-Ming Che
DOI: 10.1039/C2OB25753J

The inside cover highlights the work of Prasat Kittakoop et al. on the isolation, characterization, and biological activities of a novel tricyclic polyketide, 2 of its biosynthetic congeners as well as austdiol, a known azaphilone, from the endophytic fungus Dothideomycete sp., which was isolated from the Thai medicinal plant, Tiliacora triandra.

A novel tricyclic polyketide and its biosynthetic precursor azaphilone derivatives from the endophytic fungus Dothideomycete sp
Sarath P. D. Senadeera, Suthep Wiyakrutta, Chulabhorn Mahidol, Somsak Ruchirawat and Prasat Kittakoop
DOI: 10.1039/C2OB25959A

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Crack open this week’s issue over your coffee break and have a read…

On the front cover:

Strap yourself in with this week’s front cover highlighting the work of Ishwar Singh and co-workers who have developed a fast, strain promoted cycloaddition as a tool for RNA conjugation on the solid phase exploiting the cycloaddition of a series of RNA-cyclooctynes with both azide (strain-promoted azide–alkyne cycloaddition) and nitrile oxide dipoles (strain-promoted nitrile oxide–alkyne cycloaddition). Singh et al. say that the reaction is compatible with 2’-OMe blocking as well as with 2’-O-TBDMS protection on the ribose moieties of the sugar.

Fast RNA conjugations on solid phase by strain-promoted cycloadditions
Ishwar Singh, Colin Freeman, Annemieke Madder, Joseph S. Vyle and Frances Heaney
DOI: 10.1039/C2OB25628B

On the inside front cover:

Ming-Jung Wu and colleagues, National Sun Yat-sen University, have developed an efficient synthetic method to convert enynylpyrazoles to pyrazolo[1,5-a]pyridines and 6-iodopyrazolo[1,5-a]pyridines by gold-catalyzed cyclisation and iodinemediated cyclisation reactions, respectively. Wu et al. go on to demonstrate the synthetic utility of this by preparing a p38 kinase inhibitor.

Au(I)-catalyzed and iodine-mediated cyclization of enynylpyrazoles to provide pyrazolo[1,5-a]pyridines
Hung-Chou Wu, Chia-Wen Yang, Long-Chih Hwang and Ming-Jung Wu
DOI: 10.1039/C2OB25973G

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