Archive for November, 2012

Chemical biology and medicinal: New anticancer compounds

Scientists in Canada have reported the anti-leukaemia activity of four new prodigiosin analogues in vitro in a cancer cell line and in vivo in a zebrafish model. Prodigiosin is the parent member of a family of tripyrrolic natural products isolated from bacteria.

Graphical Abstract

Investigations regarding the utility of prodigiosenes to treat leukemia
Deborah A. Smithen, A. Michael Forrester, Dale P. Corkery, Graham Dellaire, Julie Colpitts, Sherri A. McFarland, Jason N. Berman and Alison Thompson
Org. Biomol. Chem., DOI: 10.1039/C2OB26535D

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Organic & Biomolecular Chemistry issue 46: achiral supramolecular stacks & heteroaromatic α-hydroxy esters

Guess what…. yes you got it, it’s Organic & Biomolecular Chemistry time! This week’s issue has 1 Perspective, 5 Communications and 17 Papers for your reading pleasure.

Front cover:

Put your hands together for this very nice image highlighting the work of David B. Amabilino and colleagues. Amabilino et al. use the induction of chirality in achiral aggregates of an oligo(p-phenylenevinylene) to detect the enantiomeric excess in acids used in the resolution of chiral compounds. These achiral supramolecular stacks can detect the enantiomeric excess of substoichiometric amounts different organic acids.

Sensitive detection of enantiomeric excess in different acids through chiral induction in an oligo(p-phenylenevinylene) aggregate
François Riobé, Albertus P. H. J. Schenning and David B. Amabilino
DOI: 10.1039/C2OB26411K

Inside cover:

This image of seaside chemistry is courtesy of Ming-Hua Xu and co-workers at Shanghai Institute of Materia Medica. Xu et al. present their work on developing a highly efficient and enantioselective route to quaternary carbon-containing heteroaromatic α-hydroxy esters. Xu et al. employ the catalytic asymmetric 1,2-addition of arylboronic acids to obtain these heteroaryl α-ketoesters.

Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters
Hui Wang, Ting-Shun Zhu and Ming-Hua Xu
DOI: 10.1039/C2OB26316E

Hot articles in this issue:

Reduction of metal ions by boranephosphonate DNA
Subhadeep Roy, Magdalena Olesiak, Petra Padar, Heather McCuen and Marvin H. Caruthers

The bacterial second messenger c-di-GMP: probing interactions with protein and RNA binding partners using cyclic dinucleotide analogs
Carly A. Shanahan and Scott A. Strobel

As always the articles featured on the covers are free to access for 6 weeks, and the HOT articles are free for 4!

For all this and much, much more take a look at the issue online today!

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Reduction of metal ions by boranephosphonate DNA

In this HOT communication Marvin H. Caruthers and co-workers from the University of Colorado show that oligodeoxyribonucleotides bearing boranephosphonate linkages (bpDNA) are able to reduce a variety of metal ions whilst producing nanoparticles. Carauthers et al. discovered that during the reduction of metal ions in protic solvents, the B–P bond undergoes solvolysis and generates phosphate diesters (in water) or triesters (in alcohols).

To highlight the utility of this reaction Caruthers et al. synthesised an oligomer containing an O-methyl phosphate triester linkage, which cannot be prepared via usual methods of DNA synthesis as such triesters are base labile.

Caruthers et al. believe that, in addition to bpDNA‘s potential applications in the construction of DNA templated metallic nanostructures, the new reactivity of boranephosphonates shown can be exploited as a general method for the introduction of a variety of functionalities onto the DNA backbone via phosphate triesters.

Intrigued? Read this Communication for free for the next 4 weeks to find out more!

This Communication is part of the Nucleic acids: new life, new materials collection. Why not take a look at similar work and let us know what you think here on the blog or on Twitter.

Reduction of metal ions by boranephosphonate DNA
Subhadeep Roy, Magdalena Olesiak, Petra Padar, Heather McCuen and Marvin H. Caruthers
DOI: 10.1039/C2OB26661J

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The bacterial second messenger c-di-GMP: probing interactions with protein and RNA binding partners using cyclic dinucleotide analogs – a HOT review

One of the essential capabilities of bacteria for their continued survival is the ability to adapt and change to reflect the changing environment in which they reside. One way in which they achieve this is through the second messenger signalling molecule bis-(3′–5′)-cyclic dimeric guanosine monophosphate (c-di-GMP), which facilitates behaviour adaptions.

c-di-GMP is found throughout the bacterial domain and plays a vital role in regulating the transition between the motile planktonic lifestyle and the sessile biofilm forming state. It also controls the virulence response of pathogenic organisms and is thought to be connected to quorum sensing, the process by which bacteria communicate with each other.

This HOT review from Scott A. Strobel and Carly A. Shanahan, Yale University, summarises the current state of knowledge and understanding of c-di-GMP signalling in bacteria with a focus on protein and RNA binding partners of the second messenger. Efforts towards the synthesis of c-di-GMP and its analogues are discussed as well as studies aimed at targeting these binding partners with synthetic dinucleotide analogues.

To find out more about this messenger molecule read this review taken from our Nucleic acids: new life, new materials collection.

Enjoy free access for 4 weeks, so download it today.

The bacterial second messenger c-di-GMP: probing interactions with protein and RNA binding partners using cyclic dinucleotide analogs
Carly A. Shanahan and Scott A. Strobel
DOI: 10.1039/C2OB26724A

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