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Archive for the ‘Hot articles’ Category

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

02 Nov 2012

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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Organic & Biomolecular Chemistry issue 45: poisonous frogs, spirocyclic alkaloids & cycloadditions

31 Oct 2012

Issue 45 of Organic & Biomolecular Chemistry is now online, so hop to it and take a cheeky peek….

Featuring in the issue this week:

Leaping on to the front cover is this image (right) from Andrew B. Holmes, Annabella F. Newton and colleagues. The cover highlights the work of Holmes et al. exploring the synthesis of the histrionicotoxin family, which includes some interesting investigations into the intriguing observed regioselectivity of the dipolar cycloaddition during the key cascade hydroxylamine-alkyne cyclisation/nitrone cycloaddition to form the azaspirocyclic core.

Intramolecular nitrone dipolar cycloadditions: control of regioselectivity and synthesis of naturally-occurring spirocyclic alkaloids
Alastair J. Hodges, Joseph P. Adams, Andrew D. Bond, Andrew B. Holmes, Neil J. Press, Stephen D. Roughley, John H. Ryan, Simon Saubern, Catherine J. Smith, Michael D. Turnbull and Annabella F. Newton
DOI: 10.1039/C2OB26333E

The inside cover of this week’s issue (left) features the work of Feng Shi and co-workers from Henan University. Shi et al. re-examine the use of the Kobayashi benzyne precursor in the [3 + 2] cycloaddition of arynes with 3-oxidopyridinium species, for the first time in 16 years, expanding investigations further than ever before.

Aryne cycloaddition with 3-oxidopyridinium species
Hailong Ren, Chunrui Wu, Xiuxiu Ding, Xiaoge Chen and Feng Shi
DOI: 10.1039/C2OB26519B

Both of these papers have been highlighted as being HOT chemistry by the reviewers, and they are both FREE to access for the next 6 weeks, so enjoy!

Also in this issue: 6 Communications and a further 14 papers full of great content.

Read the complete issue now…

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Issue 43 of OBC online now!

17 Oct 2012

Issue 43 of Organic & Biomolecular Chemistry has arrived, and featuring in this week’s issue:

On the front cover:

A HOT Communication from Xiangbao Meng, Zhongjun Li and colleagues from Peking University presenting a convenient, metal-free method for the intramolecular oxidative aminofluorination of unactivated terminal alkenes. This new transformation represents an efficient method for the preparation of fluorine containing cyclic amines.

Metal-free intramolecular aminofluorination of alkenes mediated by PhI(OPiv)2/hydrogen fluoride–pyridine system
Qing Wang, Wenhe Zhong, Xiong Wei, Maoheng Ning, Xiangbao Meng and Zhongjun Li
DOI: 10.1039/C2OB26664D

On the inside cover:

A Communication from Jacek Jemielity and co-workers, University of Warsaw, which is part of OBC’s Nucleic acids: new life, new materials web collection. Jemielity et al. have developed a chemoenzymatic method for obtaining RNAs that are specifically labelled with biotin at the 5′ m7G cap moiety.

Synthesis of biotin labelled cap analogue – incorporable into mRNA transcripts and promoting cap-dependent translation
Jacek Jemielity, Maciej Lukaszewicz, Joanna Kowalska, Jakub Czarnecki, Joanna Zuberek and Edward Darzynkiewicz
DOI: 10.1039/C2OB26060C

Also in this issue – 5 additional HOT articles:

Concise and efficient syntheses of preQ1 base, Q base, and (ent)-Q base
Hans-Dieter Gerber and Gerhard Klebe

Inter- and intramolecular reactions of 1-deoxy-1-thio-1,6-anhydrosugars with α-diazoesters: synthesis of the tagetitoxin core by photochemical ylide rearrangement
Anne J. Price Mortimer, Julien R. H. Plet, Oluwafunsho A. Obasanjo, Nikolas Kaltsoyannis and Michael J. Porter

Synthesis and evaluation of novel 3-C-alkylated-Neu5Ac2en derivatives as probes of influenza virus sialidase 150-loop flexibility
Mark von Itzstein et al.

Synthesis and hybridization properties of oligonucleotides modified with 5-(1-aryl-1,2,3-triazol-4-yl)-2′-deoxyuridines
Mamta Kaura, Pawan Kumar and Patrick J. Hrdlicka

A cucurbit[8]uril sponge
Vijayakumar Ramalingam, Sharon K. Kwee, Lisa M. Ryno and Adam R. Urbach

Read the issue today! The articles on the covers are free to access for 6 weeks, and the HOT articles are free to access for 4 weeks!

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Concise and efficient syntheses of preQ1 base, Q base, and (ent)-Q base

17 Oct 2012

In this HOT OBC paper from the ‘Nucleic acids: new life, new materials’ web collection, short and high-yielding syntheses for the nucleobases preQ1 base, Q base, and (ent)-Q base are described based on cheap and readily available starting compounds. For the latter two bases, Hans-Dieter Gerber and Gerhard Klebe use preQ1 as a central synthon and nucleophilic substitution reactions with appropriately decorated halocyclopentenyl synthons to produce the desired bases.

For the detailed discussion and reaction analysis download the paper, it is free to do so for 4 weeks!

Concise and efficient syntheses of preQ1 base, Q base, and (ent)-Q base
Hans-Dieter Gerber and Gerhard Klebe
DOI: 10.1039/C2OB26387D

Liked that? Then why not have a look at the rest of the ‘Nucleic acids: new life, new materials’ web collection.

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HOT article: Inter- and intramolecular reactions of 1-deoxy-1-thio-1,6-anhydrosugars with α-diazoesters: synthesis of the tagetitoxin core by photochemical ylide rearrangement

16 Oct 2012

In this HOT paper Michael J. Porter and colleagues at University College London report the synthesis of the core structure of tagetitoxin using a novel photochemical 1,2-Stevens rearrangement. The method presented by Porter et al. uses the carbene-mediated ring expansion of a bicyclic monothioacetal, through the intermediacy of a sulfonium ylide.

To see all the experimental and mechanistic details download the paper today. It will be free to access for 4 weeks!

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Novel 3-C-alkylated-Neu5Ac2en derivatives as probes of influenza virus sialidase 150-loop flexibility

15 Oct 2012

Mark von Itzstein and co-workers have synthesised a series of novel C3 C-alkylated Neu5Ac2en derivatives, which by virtue of the substituent extending from C3 are probes of 150-loop flexibility in influenza virus sialidases.

Currently there is speculation as to what factors determine or affect loop flexibility in influenza A virus sialidases. The compounds described by Mark von Itzstein et al. in this HOT paper provide a way to probe sialidases for this flexibility and should help to elucidate the generality of 150-loop flexibility across all influenza virus sialidases, the factors that affect loop flexibility, and potentially the functional roles this flexibility may play.

This article is free to download for 4 weeks so find out more by reading the paper now.

Synthesis and evaluation of novel 3-C-alkylated-Neu5Ac2en derivatives as probes of influenza virus sialidase 150-loop flexibility
Santosh Rudrawar, Philip S. Kerry, Marie-Anne Rameix-Welti, Andrea Maggioni, Jeffrey C. Dyason, Faith J. Rose, Sylvie van der Werf, Robin J. Thomson, Nadia Naffakh, Rupert J. M. Russell and Mark von Itzstein
DOI: 10.1039/C2OB25627D

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Synthesis and hybridization properties of modified oligonucleotides – a HOT Communication from Patrick J. Hrdlicka

15 Oct 2012

In this HOT Communication Patrick J. Hrdlicka and colleagues at University of Idaho study the hybridization properties of oligonucleotides, which are modified with 5-(1-aryl-1,2,3-triazol-4-yl)-2′-deoxyuridine monomers featuring three differentially sized aromatic moieties at the 1-position of the triazole ring.

These modified oligonucleotides modified with consecutive show a strong thermal affinity and binding specificity toward RNA targets, due to the formation of stabilizing chromophore arrays in the major groove.

This Communication can be downloaded for free for 4 weeks.

This work is also part of the OBC collection on ‘Nucleic acids: new life, new materials‘, so for related articles have a browse through the collection.

Synthesis and hybridization properties of oligonucleotides modified with 5-(1-aryl-1,2,3-triazol-4-yl)-2′-deoxyuridines
Mamta Kaura, Pawan Kumar and Patrick J. Hrdlicka
DOI: 10.1039/C2OB26717A

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HOT Communication – A cucurbit[8]uril sponge

12 Oct 2012

In this HOT Communication Adam R. Urbach and colleagues, Trinity University, present a convenient approach for the quantitative removal of the synthetic host cucurbit[8]uril from aqueous mixtures using a sepharose resin coated in memantine groups to selectively isolate cucurbit[8]uril in the presence of competing hosts and guests. The “cucurbit[8]uril sponge” can separate cucurbit[8]uril from cucurbit[6]uril and reverse the cucurbit[8]uril-mediated dimerization of peptides.

This communication is free to access for the next 4 weeks!

A cucurbit[8]uril sponge
Vijayakumar Ramalingam, Sharon K. Kwee, Lisa M. Ryno and Adam R. Urbach
DOI: 10.1039/C2OB26774H

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Taking a look at this week’s issue of Organic & Biomolecular Chemistry

11 Oct 2012

Organic & Biomolecular Chemistry issue 42

On the front cover:

We have this HOT article from Marcos N. Eberlin and colleagues studying corrole isomers using traveling wave ion mobility mass spectrometry and collision induced dissociation experiments. The isomers had subtle structural changes, promoted by exchange of nitrogen and carbon atoms in the corrole ring, and significant differences in the shapes and charge distributions of the protonated molecules were found to lead to contrasting gas phase mobilities.

Corrole isomers: intrinsic gas-phase shapes via traveling wave ion mobility mass spectrometry and dissociation chemistries via tandem mass spectrometry
Maíra Fasciotti, Alexandre F. Gomes, Fabio C. Gozzo, Bernardo A. Iglesias, Gilberto F. de Sá, Romeu J. Daroda, Motoki Toganoh, Hiroyuki Furuta, Koiti Araki and Marcos N. Eberlin
DOI: 10.1039/C2OB26209F

On the inside cover:

A Perspective by Xuefeng Jiang, Jason S. Chen and colleagues, on the thermodynamic driving force of many synthetic transformations – gas extrusion. The review focuses on gas expulsion in key reactions within natural products total syntheses, selected from the past two decades. Included are transformations that generate sulfur dioxide, carbon dioxide, carbonyl sulfide, or nitrogen through polar, radical, pericyclic, photochemical, or organometallic mechanisms.

Gas extrusion in natural products total synthesis
Xuefeng Jiang, Lei Shi, Hui Liu, Akbar H. Khan and Jason S. Chen
DOI: 10.1039/C2OB26152A

There is also:

Another HOT article on the efficient synthesis of N-(buta-2,3-dienyl) amides from terminal N-propargyl amides and their synthetic potential towards oxazoline derivatives by Shengming Ma et al., 1 Communication and 16 more Papers… read them all in OBC issue 42 – it’s online now.

And don’t forget, the cover articles will be free to access for the next 6 weeks!

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N-(buta-2,3-dienyl) amide synthesis, combined with palladium catalysis leads to oxazolines

08 Oct 2012

In this OBC HOT article Shengming Ma and co-workers report the efficient synthesis of N-(buta-2,3-dienyl) amides and their application towards the efficient synthesis of oxazolines under palladium catalysis.

Read the article to find out more about the reaction conditions and yields involved in this synthesis…. FREE to access for 4 weeks!

Efficient synthesis of N-(buta-2,3-dienyl) amides from terminal N-propargyl amides and their synthetic potential towards oxazoline derivatives
Bo Chen, Nan Wang, Wu Fan and Shengming Ma
DOI: 10.1039/C2OB26291F

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