Archive for the ‘Hot articles’ Category

Review on microwave synthesis of small molecules to target TB, HIV/AIDS, malaria and hepatitis C

Mats Larhed and colleagues from the University of Uppsala provide an extremely accessible introduction to microwave synthesis in this review article, demonstrating the use of single-mode microwave synthesis for laboratory-scale preparation of small molecules.  They focus of the synthesis of potential treatments of four of the world’s most infectious diseases; tuberculosis, HIV/AIDS, malaria and hepatitis C.


Microwave-assisted synthesis of small molecules targeting the infectious diseases tuberculosis, HIV/AIDS, malaria and hepatitis C
Johan Gising, Luke R. Odell and Mats Larhed
DOI: 10.1039/C2OB06833H

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Mouth bacteria makes metabolite that could prevent yeast infections

A bacteria present in the mouth – Streptococcus mutans – has been shown to generate the metabolite mutanobactin A by scientists from the US. They found that the metabolite inhibits biofilms formed by the fungal oral pathogen Candida albicans, which causes yeast infections.

In biofilms, pathogens are less susceptible to antibiotics, so this finding could have implications for treating yeast infections.

Fungal biofilm inhibitors from a human oral microbiome-derived bacterium
Xiaoru Wang, Lin Du, Jianlan You,  Jarrod B. King and Robert H. Cichewicz
DOI: 10.1039/C2OB06856G

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Multivalent scFvs, mitomycin C stereochemistry, peptide dendrimers and NET ligands in Issue 8

On the cover of Issue 8 we have two cancer-related articles from Jacquelyn Gervay-Hague (University of California Davis) on multivalent single chain variable fragments with increased tumor-associated antigen affinity and from Federico Gago (Universidad de Alcalá) modelling the binding of mitomycin C and analogues to DNA.

A general chemical synthesis platform for crosslinking multivalent single chain variable fragments
Joan G. Schellinger, Avinash Kudupudi, Arutselvan Natarajan, Wenjun Du, Sally J. DeNardo and Jacquelyn Gervay-Hague
DOI: 10.1039/C0OB01259A

Rationale for the opposite stereochemistry of the major monoadducts and interstrand crosslinks formed by mitomycin C and its decarbamoylated analogue at CpG steps in DNA and the effect of cytosine modification on reactivity
Juan A. Bueren-Calabuig, Ana Negri, Antonio Morreale and Federico Gago
DOI: 10.1039/C1OB06675G

The issue also contains a review from Jean-Louis Reymond and Tamis Darbre on combinatorial libraries of peptide and glycopeptide dendrimers and hot papers on creating (D)-sugars from (L)-amino acids from Paul Clarke and stilbazolium dimers as NET ligands from James N. Wilson.

View the issue

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HOT article: (D)-sugars from (L)-amino acids – a step closer to understanding the origin of life

A conundrum for anyone studying the prebiotic world is how chirality first occurred, and why D-sugars are the natural isomers, whereas natural amino acids have the L-configuration. In this hot paper Paul Clarke and Christopher Hayes from the Universities of York and Nottingham have shown how carbohydrates could have formed in prebiotic conditions by producing (D)-erythrose and (D)-threose sugars with (L)-amino acid catalysts.

Having first used proline esters to catalyse the aldol reaction of TIPS-protected glycolaldehyde in water with good yields and moderate diastereo- and enantioselectivity, the group hypothesised that other proteinogenic amino acids (i.e. amino acids found in proteins) could also catalyse this reaction.  Using N-methyl derivatives of the amino acid esters of (L)-alanine, (L)-leucine and (L)-valine they were able to produce the expected sugars, but were surprised to see that the (D)-enantiomer was the major product in all reactions. “This offers one potential explanation to account for the relationship between (L)-amino acids and (D)-sugars in nature” concludes Clarke.

This remarkable find has obviously generated a lot of interest in both scientific and the wider press: see articles in The Daily Mail, The Huffington Post, on Science Daily or the press release from University of York.

Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions
Laurence Burroughs, Paul A. Clarke, Henrietta Forinto, James A. R. Gilks, Christopher J. Hayes,  Matthew E. Vale , William Wade and Myriam Zbytniewski
DOI: 10.1039/C1OB06798B

This article is also part of our joint web theme issue with ChemComm on Organocatalysis and as with all our hot articles will be free to access for 4 weeks.

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Synthesising ureas from CO2, recognition of oxoanions and cross-metathesis for heterocycles in Issue 7

The cool images on this week’s cover are from Giuseppe Resnati, NFMLab, and James C. Anderson, UCL.

Resnati and colleagues have conducted an NMR study of phosphate oxoanion binding of a 2-iodo-imidazolium receptor with charge assisted halogen bonding, finding a surprisingly strong binding constant for phosphate anions, their work is highlighted on the outside front cover.

2-Iodo-imidazolium receptor binds oxoanions via charge-assisted halogen bonding
Massimo Cametti, Kari Raatikainen, Pierangelo Metrangolo, Tullio Pilati, Giancarlo Terraneo and Giuseppe Resnati
DOI: 10.1039/C1OB06524F

On a completely different topic, Anderson and Moreno have been using CO2 to produce ureas at ambient conditions, using 12- and 14- electron titanium imido complexes:

Synthesis of ureas from titanium imido complexes using CO2 as a C-1 reagent at ambient temperature and pressure
James C. Anderson and Rafael Bou Moreno
DOI: 10.1039/C1OB06576A

As well as these the issue also contains a review from Tim Donohoe on olefin cross-metathesis for heterocycle synthesis and plenty of other hot articles, take a look…

Hot articles in this issue:

Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: preparation and computational analysis of non symmetrical zwitterionic biscyanines
Theodosia A. Ioannou, Panayiotis A. Koutentis, Harry Krassos, Georgia Loizou and Daniele Lo Re
DOI: 10.1039/C1OB06622F

Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation
B. V. Subba Reddy, Prashant Borkar, J. S. Yadav, P. Purushotham Reddy, A. C. Kunwar, B. Sridhar and René Grée
DOI: 10.1039/C1OB06489D

Chemoenzymatic synthesis of a mixed phosphine–phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes
Derek R. Boyd, Mark Bell, Katherine S. Dunne, Brian Kelly, Paul J. Stevenson, John F. Malone and Christopher C. R. Allen
DOI: 10.1039/C1OB06599H

James C. Anderson and Rafael Bou Moreno
Org. Biomol. Chem., 2012, 10, 1334-1338
DOI: 10.1039/C1OB06576A

Certain 12- and 14- electron titanium imido complexes

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Imaging Norepinephrine transporters (NET) with self-reporting dyes

One area of research developed in Dr James N. Wilson‘s lab at the University of Miami (Florida, USA) is aimed at elucidating the complex molecular mechanisms of intercellular communication, via the development of fluorescent analogues of neuroactive compounds.

In their latest OBC communication,  Wilson et al. describe the synthesis, characterization and interaction of cell lines with novel dimeric stilbazolium-based dyes that probe the functional limit of norepinephrine transport (NET) in cells. Upon exposure to different NET proteins, these environmentally sensitive dyes turn on the fluorescence and their binding to NET can be monitored using fluorescence microscopy

This article will be FREE to access for the next 4 weeks.
Why not read it now and let us know what you think by posting a comment below!

Probing the functional limits of the norepinephrine transporter with self-reporting, fluorescent stilbazolium dimers
Erika L. Smith, Adrienne S. Brown, Edward Adjaye-Mensah and James N. Wilson
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06796J, Communication

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Cyclocondensation reactions of the heterocyclic scaffold benzotriazinone lead to several highly coloured acenes

In this OBC Hot Article, Panayiotis Koutentis and co-workers at the University of Cyprus show how 1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one reacts with various bisnucleophiles to give a variety of deeply coloured polyazaacenes, including two zwitterionic analogues.

 

Read the article to find out more about the preparation, mechanistic considerations and photophysical studies of these new heterocyclic ring systems derived from benzo[1,2,4]triazin-7-ones.

FREE to access for a period of 4 weeks!




Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: preparation and computational analysis of non symmetrical zwitterionic biscyanines
Theodosia A. Ioannou, Panayiotis A. Koutentis, Harry Krassos, Georgia Loizou and Daniele Lo Re
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06622F, Paper

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Issue 6 online – including water-binding aquafoldamers, fluorinated probes and glycosylated 5-hydroxylysine

On the outside front cover of this week’s issue is a hot article from Huaiqing Zhao, National University of Singapore, et al. on a series of water-binding aquafoldamers with potential use in recognizing topologically diverse larger water clusters and as synthetic water channels. This article is part of our forthcoming themed issue on Foldamer Chemistry.

Synthesis, structural investigation and computational modelling of water-binding aquafoldamers
Huaiqing Zhao, Wei Qiang Ong, Xiao Fang, Feng Zhou, Meng Ni Hii, Sam Fong Yau Li, Haibin Su and Huaqiang Zeng
DOI: 10.1039/C1OB06609A

The inside front cover is work from Jonathan Guimond-Tremblay, Université Laval, et al. on the synthesis of three monofluorinated dimyristoylphosphatidylcholine derivatives for use as probes in 19F NMR studies to study the effects of drugs and peptides on model membranes.

Synthesis and properties of monofluorinated dimyristoylphosphatidylcholine derivatives: Potential fluorinated probes for the study of membrane topology
Jonathan Guimond-Tremblay, Marie-Claude Gagnon, Jozy-Ann Pineault-Maltais, Vanessa Turcotte, Michèle Auger and Jean-François Paquin
DOI: 10.1039/C2OB06570C

The issue also includes a review on the synthesis of glycosylated (2S,5R)-hydroxylysine from Margaret Brimble and coworkers and a hot article from Valentina Cerulli et al., on a highly diastereoselective Ugi multicomponent reaction

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Hot Emerging Area article: olefin cross-metathesis for the synthesis of heteroaromatic compounds

Timothy Donohoe et al. from the University of Oxford review recent developments in the synthesis of furan, pyrrole and pyridine heterocycles via cross-metathesis methods in this Emerging Area article.

It’s free to access for 4 weeks, so take a look…

Olefin cross-metathesis for the synthesis of heteroaromatic compounds
Timothy J. Donohoe, John F. Bower and Louis K. M. Chan
DOI: 10.1039/C2OB06659A

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HOT: chemoenzymatic synthesis of a mixed phosphine–phosphine oxide organocatalyst and its applications

This OBC Hot Article by Paul J. Stevenson and co-workers at Queens University (Belfast) and Celtic Catalysts Ltd (Dublin) highlights the chemoenzymatic synthesis of a Lewis basic phosphine–phosphine oxide organocatalyst from a cis-dihydrodiol metabolite of bromobenzene.

Of particular interest is the impressively facile Arbuzov [2,3]-sigmatropic rearrangement reaction that the team observed – a pivotal step for this synthesis.

  • Find out about the applications of this new catalyst…
  • Read the article for Free for the next 4 weeks…

Reference
Chemoenzymatic synthesis of a mixed phosphine–phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes
Derek R. Boyd, Mark Bell, Katherine S. Dunne, Brian Kelly, Paul J. Stevenson, John F. Malone and Christopher C. R. Allen
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06599H, Paper

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